Category: tetrahydroisoquinoline

As a common heterocyclic compound, it belong tetrahydroisoquinoline compound,6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,215798-19-9,Molecular formula: C9H11BrClN,mainly used in chemical industry, its synthesis route is as follows.,215798-19-9

Step C: Preparation of Intermediate (R)-6-(4-(2-(2-Methylpyrrolidin-1- yl)ethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline. To a round-bottom flask was added 6-bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.00 g, 8.05 mmol), (R)-4-(2-(2-methylpyrrolidin- 1 -yl)ethyl)phenylboronic acid (2.063 g, 8.85 mmol), tetrakis(triphenylphosphine)palladium (0) (0.279 g, 0.24 1 mmol), benzene (30.00 mL), ethanol (10.00 mL), and 2.0 M aqueous solution of sodium bicarbonate(8.05 mL, 16.09 mmol). The reaction mixture was refluxed for 6 h. Upon completion, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated. The residue was taken up in 1 M HC1 solution and washed with ethyl acetate. The aqueous layer was basified with 10% aqueous NaOH to pH-4 1, extracted with ethyl acetate, and concentrated. The residue was purified by silica gel column,eluting with 5-10% 2.0 M ammonia in methanol/DCM to give a yellow solid (1.20 g). LCMSm/z = 321.4 [M+H] ?H NMR (400 MHz, DMSO-d6) oe ppm 0.99-1.04 (m, 3H), 1.22-1.33 (m,1H), 1.59-1.69 (m, 2H), 1.81-1.92 (m, 1H), 2.13 (q, J= 8.67 Hz, 1H), 2.20-2.34 (m, 2H), 2.65-2.83 (m, 5H), 2.94-3.04 (m, 3H), 3.10-3.18 (m, 1H), 3.91 (s, 2H), 7.09 (d, J= 8.08 Hz, 1H),7.29 (d, J = 8.08 Hz, 2H), 7.33-7.40 (m, 2H), 7.53 (d, J = 8.08 Hz, 2H).

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,belong tetrahydroisoquinoline compound

Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; REN, Albert; SEMPLE, Graeme; TRAN, Thuy-Anh; WEI, Zheng; GROTTICK, Andrew J.; MILLS, David M.; SMITH, Brian M.; WO2014/28322; (2014); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belong tetrahydroisoquinoline compound,5-Bromo-1,2,3,4-tetrahydroisoquinoline,81237-69-6,Molecular formula: C9H10BrN,mainly used in chemical industry, its synthesis route is as follows.,81237-69-6

Triphosgene (37 mg, 0.12 mmol) was added into a cold (0 C.) solution of 3-hydroxy-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2,4-dione (55 mg, 0.36 mmol), N,N-diisopropylethylamine (0.06 mL, 0.47 mmol) and dichloromethane (3 mL). The reaction mixture was allowed to come to room temperature and stirred for 30 minutes. The resulting solution was added dropwise into a cold (0 C.) solution of 5-bromo-1,2,3,4-tetrahydroisoquinoline (50 mg, 0.24 mmol), N,N-diisopropylethylamine (0.06 mL, 0.47 mmol) and dichloromethane (3 mL). The reaction mixture was allowed to come to room temperature and stirred for 1 hour. Then, the reaction was diluted in dichloromethane (25 mL) and washed with water (2*15 mL) and brine. The organic extracts were dried over anhydrous NaSO4. The solvents were removed under vacuum and the residue was purified on silica gel (Biotage; eluting solvents hexanes:EtOAc 3/1 ratio) to afford 6,6-dimethyl-2,4-dioxo-3-azabicyclo[3.1.0]hexan-3-yl 5-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate as colorless solid (56 mg, 65% yield); 1H NMR (400 MHz, CDCl3) delta ppm 7.48-7.46 (m, 1H), 7.10-7.04 (m, 2H), 4.75-4.63 (m, 2H), 3.83-3.74 (m, 2H), 2.99-2.95 (m, 2H).

With the synthetic route has been constantly updated, we look forward to future research findings about 5-Bromo-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

Reference£º
Patent; Malamas, Michael; Makriyannis, Alexandros; Lamani, Manjunath; Farah, Shrouq I.; US2019/152917; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

1-Phenyl-1,2,3,4-tetrahydroisoquinoline, cas is 22990-19-8, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

A solution of 3,4-dimethoxyphenethylamine (1.1 mmol) and DIPEA (2.2 mmol) in THF (10 ml) was slowly added to a THF solution (10 ml) of triphosgene (0.44 mmol) And stirred for 30-45 minutes. Then, a solution of 1-phenyl-1,2,3,4-tetrahydroisoquinoline (1.1 mmol) in THF (10 ml) was added and stirred overnight. The salt was filtered, and the filtrate was evaporated and column chromatography (EA: Hexane) was carried out to obtain the title compound.

22990-19-8, As the rapid development of chemical substances, we look forward to future research findings about 22990-19-8

Reference£º
Patent; The Industry & Academic Cooperation in Chungnam National University (IAC); Jung, Sang-Hun; Woo, Sun-Hee; Kim, Sang- Kyum; Jeon, Eun-Seok; Lee, Yu-Jung; Meunikam, Manoj; Jalani, Hiteshkumar; Sharma, Niti; (205 pag.)KR2016/108281; (2016); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belong tetrahydroisoquinoline compound,6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride,215798-14-4,Molecular formula: C10H11ClF3N,mainly used in chemical industry, its synthesis route is as follows.,215798-14-4

Step B: N-[2,6-Dimethyl-4-(6-trifluoromethyl-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-3,3-dimethyl butanamide Bis(dibenzylidineacetone)palladium (390 mg, 0.68 mmol) and (2′-dicyclohexyl phosphanyl-biphenyl-2-yl)-dimethylamine (800 mg, 2.0 mmol) were added to dry toluene (150 mL purged with argon) and stirred for 30 minutes under argon. Potassium tert-butoxide (4.75 mg, 42.3 mmol), 6-Trifluoromethyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride salt (4.82 g, 20.3 mmol) and N-(4-bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide (5 g, 16.8 mmol) were then added, and the reaction mixture was stirred at 80 C. overnight. The reaction mixture was then cooled to room temperature and recrystallized from toluene to afford the title compound as a solid. (5.55 g, 79%).1H NMR (DMSO-d6, 500 MHz) delta 1.03 (s, 9H), 2.09 (s, 6H), 2.15 (s, 2H), 2.98 (t, J=5.0 Hz, 2H), 3.52 (t, J=6.0 Hz, 2H), 4.40 (s, 2H), 6.71 (s, 2H), 7.45 (d, J=8.0, 1H), 7.52 (m, 2H), 8.87 (s, 1H).

With the synthetic route has been constantly updated, we look forward to future research findings about 6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride,belong tetrahydroisoquinoline compound

Reference£º
Patent; Valeant Pharmaceuticals North America; US2008/139610; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

33537-99-4,33537-99-4, 6-Chloro-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 5-bromo-2-pyrimidin-2-yl-pyrimidine (150 mg, 633 muiotaetaomicron, the product of step 3 in Example 1), 6-chloro-l,2,3,4-tetrahydroisoquinoline (127 mg, 759 muiotaetaomicron), Ruphos (11.8 mg, 25.3 muiotaetaomicron), Pd2(dba)3 (11.6 mg, 12.7 muiotaetaomicron) and sodium iert-butoxide (122 mg, 1.27 mmol) in dioxane (10 mL) was heated at 110 C with stirring overnight. After being cooled to rt, the resulting mixture was diluted with H20 and extracted with EA (50 mL) for three times. The combined EA layer was dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by prep-HPLC to give 6-chloro-2-(2-pyrimidin-2-ylpyrimidin-5-yl)-3,4-dihydro- lH-isoquinoline (10 mg) as light yellow solid. XH NMR (400 MHz, CDC13) delta ppm: 2.99 – 3.08 (m, 2 H), 3.72 (s, 2 H), 4.55 (s, 2 H), 7.15 – 7.20 (m, 1 H), 7.23 (s, 2 H), 7.31 – 7.36 (m, 1 H), 8.60 (s, 2 H), 8.96 (d, 2 H). MS obsd. (ESI+) [(M+H)+] : 324.

33537-99-4,6-Chloro-1,2,3,4-tetrahydroisoquinolinebelongs to tetrahydroisoquinoline compound, is more and more widely used in various fields. and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belong tetrahydroisoquinoline compound,7-Nitro-1,2,3,4-tetrahydroisoquinoline,42923-79-5,Molecular formula: C9H10N2O2,mainly used in chemical industry, its synthesis route is as follows.,42923-79-5

PREPARATION 212-methyl-1 ,2,3,4-tetrahydro-7-isoquinolinamineStep 1. 2-methyl-7-nitro-1 ,2,3,4-tetrahydroisoquinolineTo a mixture of formaldehyde (26 mL, 944 mmol) and HC02H (15 mL), was added 7- nitro-1 ,2,3,4-tetrahydroisoquinoline (6.32 g, 29.4 mmol). The mixture was heated at 100 C for 4 h. The reaction was then cooled to rt, poured into ice, and basified to pH 1 1 with aq. ammonia. The gummy residue which precipitated was extracted with CH2CI2 (2 x 150 mL). The combined organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The compound was loaded onto florisil and purified via flash column chromatography (ISCO, 120 g silica, 0-5% HCI/ CH2CI2) to give 2-methyl-7-nitro-1 , 2,3,4- tetrahydroisoquinoline (5 g, 84%) as an orange solid. 1 H NMR (400 MHz, DMSO-d6) delta 7.95 – 8.00 (m, 2H), 7.39 (d, J = 8.81 Hz, 1 H), 3.58 (s, 2H), 2.93 (t, J = 5.79 Hz, 2H), 2.62 (t, J = 5.92 Hz, 2H), 2.36 (s, 3H); MS (m/z) 193.1 (M+H)+.

With the synthetic route has been constantly updated, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

Reference£º
Patent; GLAXOSMITHKLINE LLC; KALLANDER, Lara, S.; LAWHORN, Brian, Griffin; PHILIP, Joanne; ZHAO, Yongdong; WO2011/88027; (2011); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO352,mainly used in chemical industry, its synthesis route is as follows.,42923-79-5

General procedure: A solution of N-heterocycle compound (0.2 mmol) and graphene oxide (GO) (8 mg) in N,N-dimethylformamide(1.0 mL) was stirred in a sealed tube under an atmosphere of argon at 150 C for 18 h. After being cooled to room temperature,the reaction mixture was filtered and washed with ethyl acetate (20 mL). Afterward, 10 mL water was added tothe solution and extracted with ethyl acetate (3 ¡Á 15 mL), the combined organic layers were dried over anhydrous Na2SO4.The solvent was evaporated under vacuum and the crude product was purified by preparative thin-layer chromatography (TLC) on silica gel with petroleum ether and ethyl acetate to achieve the pure product.

With the synthetic route has been constantly updated, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

Reference£º
Article; Ma, Juan; Zhang, Jingyu; Zhou, Xiao; Wang, Jiawei; Gong, Hang; Journal of the Iranian Chemical Society; vol. 15; 12; (2018); p. 2851 – 2860;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.215798-14-4,6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.

Step B: N-[2-Chloro-4-(6-trifluoromethyl-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-3,3-dimethylbutanamide Bis(dibenzylidineacetone)palladium (2 mg, 0.0035 mmol) and (2′-dicyclohexyl phosphanyl-biphenyl-2-yl)-dimethylamine (3.3 mg, 0.0084 mmol) were added to dry toluene (10 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (197 mg, 1.75 mmol), 6-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline hydrochloride salt (154 mg, 0.65 mmol) and N-(4-bromo-2-chloro)-3,3-dimethylbutanamide (200 mg, 0.66 mmol) were then added and the reaction mixture was stirred at 90 C. overnight. The reaction mixture was then cooled to room temperature, concentrated, and purified by thin layer chromatography (dichloromethane:methanol 5%) to afford the title compound as a solid.1H NMR (DMSO-d6, 400 MHz) delta 1.03 (s, 9H), 2.19 (s, 2H), 2.99 (t, J=8 Hz, 2H), 3.58 (t, J=8 Hz, 2H), 4.48 (s, 2H), 6.99 (dd, J=4, 8 Hz, 1H), 7.08 (d, J=4 Hz, 1H), 7.35 (dd, J=4, 8 Hz, 1H), 7.48 (dd, J=4, 8 Hz, 1H), 7.56 (m, 2H), 9.19 (s, 1H).

215798-14-4, The synthetic route of 215798-14-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Valeant Pharmaceuticals North America; US2008/139610; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.226942-29-6,6-Bromo-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

In a pressure vessel equipped with a magnetic stirring bar was added 6-bromo-l,2,3,4- tetrahydroisoquinoline (1.328 g, 6.26 mmol), and 2-chloro-4-(pyridin-3-yl)pyrimidine (1 g, 5.22 mmol) in acetonitrile (25 mL). Hunig’s base (2.73 mL, 15.66 mmol) was added and the mixture was heated to 80 C in a preheated oil bath and allowed to stir for 16 hours overnight. Reaction appears complete by LC/MS, cooled to RT and filtered solids, washed with ethyl acetate, concentrated in vacuo to a solid. Took up solid in EtOAc: heated to dissolve most material in minimum amount of solvent, filtered while hot, and allowed to cool to RT. After filtration and drying under vacuum, 1.5g (87%) of 6-bromo- 2-(4-(pyridin-3-yl)pyrimidin-2-yl)-l,2,3,4-tetrahydroisoquinoline was obtained as a light brown solid. LCMS (M+l) = 366.7 and 368.6., 226942-29-6

226942-29-6 6-Bromo-1,2,3,4-tetrahydroisoquinoline 15885183, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BOWSHER, Michael S.; DESKUS, Jeffrey; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (220 pag.)WO2018/127801; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 1-Phenyl-1,2,3,4-tetrahydroisoquinoline, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 22990-19-8, its synthesis route is as follows.,22990-19-8

Resolution of (R:S)-1 -phenyl- 1,2,3,4-tetrahydroisoquinoline (100 g) was carried out using (D)-(-)-tartaric acid in water as per the literature method known in the art (Ref 1.- J. Chem. Soc. Perkin. Trans I, (4), 869-73 (1988), Ref. 2.- Monatshefte Fur. Chemie, vol. 53-54:956-962(1929)) and diastereomeric (D)-(-)-tartaric acid salt of (1S)- 1 -phenyl- 1,2,3,4-tetrahydroisoquinoline was filtered out as a solid. The filtrate containing enantiomerically enriched (D)-(-)-tartaric acid salt of (lR)-l-phenyl-l,2,3,4- tetrahydroisoquinoline was collected and a clear aqueous solution 40 % aq. sodium hydroxide (NaOH, 85 mL) was added at room temperature when solid was precipitated. The precipitated solid was filtered and washed with water and dried. The weight of enantiomerically enriched (lR)-l-phenyl-l,2,3,4-tetrahydroisoquinoline was 61.0 g. (% Purity by HPLC-97.0 %; % Chiral purity of R-isomer -79.0 %).

With the complex challenges of chemical substances, we look forward to future research findings about 1-Phenyl-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; CADILA HEALTHCARE LIMITED; KOTHARI, Himanshu M.; DAVE, Mayank Ghanshyambhai; PANDEY, Bipin; WO2011/48607; (2011); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem