Author: Jessica.F

1,2,3,4-Tetrahydroisoquinoline, cas is 91-21-4, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.,91-21-4

1,2,3,4-tetrahydroiosquinoline (Aldrich Tl,300-5, 100 gm) (11.6 g, 84.8 mmol) is added dropwise with care to stirred ice-cold concentrated H2S04 (42.0 mL). Potassium nitrate (9.40 g. , 93 mmol) is then added in small portions, taking care that the temperature of the reaction mixture does not rise above 5 C. After stirring overnight at room temperature the dark brown reaction mixture is added carefully to a stirred ice-cold concentrated NH40H solution. The basic red reaction mixture is extracted with chloroform (three times), and the combined chloroform extracts is washed with brine and dried over anhydrous Na2S04. Evaporation of the solvent gives a dark brown oil (14.6 g) which was taken up in EtOH (65 mL) and cooled in an ice bath. Treatment of this reddish solution with concentrated HCI (11 mL) yields a viscous yellow precipitate of the hydrochloride salt which is filtered and crystallized from methanol (250 mL) to yield the product compound (2) as a solid (5.36 g, ~30% yield). Alternatively, flash chromatography may be used to purify the crude reaction mixture before crystallization.

91-21-4 is used more and more widely, we look forward to future research findings about 1,2,3,4-Tetrahydroisoquinoline

Reference£º
Patent; ENVIVO PHARMACEUTICALS, INC.; WO2005/108367; (2005); 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.877861-62-6,Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride,as a common compound, the synthetic route is as follows.,877861-62-6

Example 1methyl 2-{[1-(tert-butoxycarbonyl)-4-methylpiperidin-4-yl]carbonyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate Intermediate 1; A solution of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (0.830 g, 3.41 mmol) and triethylamine (0.792 mL, 5.68 mmol) in DMF (11.0 mL) was treated with TFFH (1.13 g, 4.26 mmol). The resulting mixture was stirred at rt for 30 min and then methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride (0.647 g, 2.84 mmol) and triethylamine (0.792 mL, 5.68 mmol) were added. The reaction mixture was stirred at rt for 2 days and then extracted with EtOAc three times. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the resulting residue by column chromatography (SiO2, 0-100% EtOAc in hexane) provided methyl 2-{[1-(tert-butoxycarbonyl)-4-methylpiperidin-4-yl]carbonyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (0.959 g, 82%). LC-MS: (FA) ES+ 439 (M+Na); 1H NMR (400 MHz, CDCl3) delta 7.85 (dd, J=10.1, 2.2 Hz, 2H), 7.19 (d, J=8.0 Hz, 1H), 4.79 (s, 2H), 3.95-3.77 (m, 5H), 3.67 (d, J=38.1 Hz, 2H), 3.21 (s, 2H), 2.92 (t, J=5.7 Hz, 2H), 2.24-2.10 (m, 2H), 1.61 (d, J=10.8 Hz, 1H), 1.44 (d, J=5.0 Hz, 10H), 1.33 (d, J=3.6 Hz, 3H).

877861-62-6 Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride 42614607, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Millennium Pharmaceuticals, Inc.; US2012/165316; (2012); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

It is a common heterocyclic compound, the tetrahydroisoquinoline compound, 6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride, cas is 215798-19-9 its synthesis route is as follows.,215798-19-9

Triethylamine (2.8ml, 20 mmol) was added to a suspension of 6-bromo-1 ,2,3,4- tetrahydroisoquinoline hydrochloride (1g, 4.0 mmol, ASW MedChem Product List) and di-tert-butyl dicarbonate (1.87ml, 8.1 mmol) in methanol (10ml) at room temperature under nitrogen. The mixture was stirred overnight and then for a further 6h. The solvent was evaporated to give a white solid, which was partitioned between DCM and saturated sodium hydrogen carbonate solution, the organic dried (hydrophobic frit), and concentrated. The residue was dried under vacuum overnight, dissolved in methanol and applied to an SCX SPE (2Og). The cartridge was eluted with methanol and the fractions combined and evaporated to give 1 ,1- dimethylethyl 6-bromo-3,4-dihydro-2(1 H)-isoquinolinecarboxylate as a pale yellow gum (1.22g). LCMS (Method formate): Retention time 1.38min, MH+ = 312 / 314.

With the complex challenges of chemical substances, we look forward to future research findings about 6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reference£º
Patent; GLAXO GROUP LIMITED; BAILEY, James, Matthew; BIT, Rino, Antonio; DEMONT, Emmanuel, Hubert; HARRISON, Lee, Andrew; JONES, Katherine, Louise; SMETHURST, Christian, Alan, Paul; WITHERINGTON, Jason; WO2010/146105; (2010); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 99365-69-2, its synthesis route is as follows.,99365-69-2

7-nitro-l,2,3,4-tetrahydro-isoquinoline hydrochloride (2.57 g) was stirred inCH2Cl2/satd. NaHCO3 for 40 min. After separation of the layers (hydrophobic frit) the solvent was evaporated and the resulting solid dissolved in EtOH (80 ml), PtO2 (112 mg) was added and the mixture was stirred under an atmosphere of hydrogen for 3h. The catalyst was removed by filtration and solvent evaporated to give 7-amino-l,2,3,4-tetrahydro-isoquinoline as a brown solid (1.73 g).

With the complex challenges of chemical substances, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reference£º
Patent; PIRAMED LIMITED; THE INSTITUTE OF CANCER RESEARCH; WO2008/125839; (2008); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

A common heterocyclic compound, the tetrahydroisoquinoline compound, name is 5-Bromo-1,2,3,4-tetrahydroisoquinoline,cas is 81237-69-6, mainly used in chemical industry, its synthesis route is as follows.

81237-69-6, A 20 mL vial was charged with 2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-151-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (0.1 g,0.332 mmol), 5-bromo-1,2,3,4-tetrahydroisoquinoline (0.083 g, 0.332 mmol), o-benzotriazol-1-yl-N,N,N’,N’-tetramethyluroniumtetrafluoroborate (0.133 g, 0.415 mmol), Hunig’s base (0.580 mL,3.32 mmol), and DMF (3 mL). The vial was sealed and stirred at room temperature. After stirring the mixture for 70.5 h, the reaction mixture was quenched withwater. The solids that formed were collected by filtration. The mother liquorwas concentrated under reduced pressure, and a second batch of solids was collected by recrystallizing from MeOH and water. 1-(5-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione (0.145 g, 0.293 mmol, 88 % yield),was isolated as an off-white solid. LC/MS: m/z 495 (M+H)+, 497.02 (M+3H)+1.935 min (method 1). 1H NMR (500 MHz, DMSO-D6) delta ppm 12.42 (s, 1H),9.22-9.27 (m, 1H), 8.18-8.31 (m, 1H), 7.84 (s, 1H), 7.09-7.59 (m, 3H),4.59-4.87 (m, 2H), 3.67-3.95 (m, 5H), 2.73-2.96 (m, 2H), 2.47-2.52 (m, 3H).

As the rapid development of chemical substances, we look forward to future research findings about 81237-69-6

Reference£º
Article; Swidorski, Jacob J.; Liu, Zheng; Yin, Zhiwei; Wang, Tao; Carini, David J.; Rahematpura, Sandhya; Zheng, Ming; Johnson, Kim; Zhang, Sharon; Lin, Pin-Fang; Parker, Dawn D.; Li, Wenying; Meanwell, Nicholas A.; Hamann, Lawrence G.; Regueiro-Ren, Alicia; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 160 – 167;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

A common heterocyclic compound, the tetrahydroisoquinoline compound, name is 6-Methoxy-1,2,3,4-tetrahydroisoquinoline,cas is 42923-77-3, mainly used in chemical industry, its synthesis route is as follows.

To a solution of 6-methoxy-1,2,3,4-tetrahydroisoquinoline (1.08 g, 6.62 mmol) dissolved DCM (16 mL) was added Pyridine 1.6 mL, 19.85 mL) and (0678) Trifluoroaceticanhydride (2.8 ml, 19.85 mmol) and allowed to react overnight at room temperature. After reaction completion, quenched with water (25 mL) and extracted with ethyl acetate (3 X 50 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuuo. Purification of the resulting crude by silica gel column chromatography provided the desired product as a colorless viscous oil in 98% yield (1.68 mg).1H NMR (400 MHz, Chloroform-d) delta 7.09- 7.01 (m, 1H), 6.79 (dt, J = 8.5, 3.0 Hz, 1H), 6.70 (dd, J = 10.3, 2.7 Hz, 1H), 4.71 (d, J = 18.6 Hz, 2H), 3.89- 3.80 (m, 2H), 3.80 (d, J = 1.5 Hz, 3H), 2.96- 2.90 (m, 2H). Yield: 98%.

42923-77-3, As the rapid development of chemical substances, we look forward to future research findings about 42923-77-3

Reference£º
Patent; SOUTHERN RESEARCH INSTITUTE; OYAGEN, INC.; ANANTHAN, Subramaniam; AUGELLI-SZAFRAN, Corinne E.; BENNETT, Ryan P.; SMITH, Harold C.; VENUKADASULA, Phanindra Krishna Mohan; (227 pag.)WO2019/133666; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

A common heterocyclic compound, the tetrahydroisoquinoline compound, name is 1,2,3,4-Tetrahydroisoquinoline,cas is 91-21-4, mainly used in chemical industry, its synthesis route is as follows.

91-21-4, All amines were purchased from Sigma-Aldrich (Merk) except7-nitro-1,2,3,4-tetrahydroisoquinoline 18 and 1-(2,4-dimethylphenyl)-N-methylmethanamine 19, the synthesis ofwhich is summarized below.On an ice bath (0 C), a 100-mL round bottom flask with 1.3 g(10 mmol) of 1,2,3,4-tetrahydroquinoline and 5mL of conc. H2SO4was allowed to stir for 10 min. To this solution, 1.1 g (10 mmol) ofKNO3 were added in small portions, taking care that the temperatureof the reaction did not rise above 5 C. The reactionwas stirredovernight and monitored by TLC (DCM/EtOH 90:10). The brownsolution was neutralized with a solution of diluted NH4OH untilpH 8 and the basic mixture was extracted with DCM (3 x 50 mL).The combined organic extracts were washed with brine (once),dried and filtered. The evaporation of the solvent affords a red oilwhich was dissolved in the minimum amount of abs. EtOH andcooled on an ice bath. The alcoholic solution was treated with2.5 mL of conc. HCl to affords a yellow precipitate of 7-nitro-1,2,3,4-tetrahydroisoquinoline 18, which was recrystallized from MeOH.Yellow solid; m.p.: 261-263 (260-262 C [57]); Yield: 32%; I.R.(nujol, cm-1): 3173; 1H NMR (CDCl3-TMS) delta: 1.86 (br s, 1H, NHdisapp. on D2O), 3.12 (t, 2H, H-4, J 8 Hz), 3.46 (t, 2H, H-3, J 8 Hz),4.37 (s, 2H, H-1), 7.36 (d, 1H, arom. H-5, J 12 Hz), 8.00 (m, 2H,arom. H-6 and H-8).

As the rapid development of chemical substances, we look forward to future research findings about 91-21-4

Reference£º
Article; Zampieri, Daniele; Fortuna, Sara; Calabretti, Antonella; Romano, Maurizio; Menegazzi, Renzo; Schepmann, Dirk; Wuensch, Bernhard; Collina, Simona; Zanon, Davide; Mamolo, Maria Grazia; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 268 – 282;,
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: C8H14ClNO325,mainly used in chemical industry, its synthesis route is as follows.,877861-62-6

: To a mixture of 6-methoxycarbonyl-l,2,3,4-tetrahydroisoquinoline hydrochloride (50 mg, 0.22 mmol) and N^V-dimethylaminopyridine (1 10 mg, 0.9 mmol) in DMF (3.2 mL) was added n- butanesulfonyl chloride (34.4 mg, 0.22 mmol). The reaction was allowed to stir at room temperature overnight. The solvent was removed in vacuo and the residue obtained was partitioned between DCE (3 x 5 mL) and saturated aqueous sodium bicarbonate (5 mL). The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated to yield a white solid. LCMS (FA) ES+ 405.

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

Reference£º
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BLACKBURN, Christopher; CIAVARRI, Jeffrey; GIGSTAD, Kenneth; XU, He; WO2010/151318; (2010); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

42923-79-5,7-Nitro-1,2,3,4-tetrahydroisoquinoline, cas is 42923-79-5, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

The mixture of 7-Nitro- 1,2,3, 4-tetrahydro-isoquinoline (1.5 g, 8.38 mmole) and 10% Pd/C (300 mg) in diethyleneglycol (5 mL) was submitted to Smith Synthesizer under microwave radiation at 220 C for 25 min. The resulting mixture was diluted with MeOH arid filtered. The filtrate was concentrated and diluted with CH2Cl2, washed with sat’a’q. ‘ NH4CI and dried over Na2SO4. After filtration and concentration, the desired compound was isolated through flash chromatography (eluted with CH2Cl2:Me0H 9: 1) as an orange solid. MS: (ES+) 145(M+H). Calc’d. for C9H8N2 – 144.07.

With the rapid development of chemical substances, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; AMGEN INC.; WO2007/48070; (2007); A2;,
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: C8H14ClNO454,mainly used in chemical industry, its synthesis route is as follows.,215798-14-4

Step 2. Synthesis of 2-(4,6-dimethoxy-5-nitropyrimidin-2-yl)-6-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline, 5b 1,8-diazabicyclo[5.4.0]undec-7-ene (0.669 g, 4.4 mmol) was added to a mixture of 4a (0.438 g, 2 mmol) and 6-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.487 g, 2.05 mmol) in DMF (5 ml) at 0 C. over 5 minutes. The mixture was stirred for an additional 5 minutes at room temperature. The mixture was washed with brine, extracted with ethyl acetate and chromatographed to yield 5b (0.76 g, 1.98 mmol, 99%).

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 INTERNATIONAL; US2008/318979; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem