Category: tetrahydroisoquinoline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.91-21-4,1,2,3,4-Tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

1,2,3,4-Tetrahydroisoquinoline (6.3 mL, 50.0 mmol) was added dropwise to a stirred ice-cold solution of concentrated H2SO4 (25 mL). KNO3 (5.6 g, 55.0 mmol) was added portionwise while maintaining the temperature below 5¡ã C. The mixture was stirred at room temperature overnight, carefully poured into an ice-cold solution of concentrated NH4OH, and then extracted three times with CHCl3. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The resulting dark brown oil was taken up into EtOH, cooled in an ice bath and treated with concentrated HCl. The yellow precipitate was collected via filtration and recrystallized from methanol to give 1,2,3,4-tetrahydro-7-nitroisoquinoline hydrochloride as yellow solid (2.5 g, 23percent). 1H NMR (400 MHz, DMSO-d6) delta 9.86 (s, 2H), 8.22 (d, J=1.6 Hz, 1H), 8.11 (dd, J=8.5, 2.2 Hz, 1H), 7.53 (d, J=8.5 Hz, 1H), 4.38 (s, 2H), 3.38 (s, 2H), 3.17-3.14 (m, 2H); HPLC ret. time 0.51 min, 10-99percent CH3CN, 5 min run; ESI-MS 179.0 m/z (MH+)., 91-21-4

The synthetic route of 91-21-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

7-Chloro-1,2,3,4-tetrahydroisoquinoline, cas is 82771-60-6, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.,82771-60-6

General procedure: To ice cold solutions of substituted-1,2,3,4-tetrahydroisoquinolines (1) (1.5 mmol) in a mixture of 2 mL of acetic acid and 2.2 mL of H2O, aqueous solutions of sodium nitrite (NaNO2, 4.5 mmol) in 1.5 mL of H2O were added drop by drop over 2 min at 0 C. in an ice-water bath. The reaction mixtures were stirred for 3 h. (0165) Thin Layer Chromatography (TLC) indicated that the reactions were complete. The reaction mixtures were extracted with CH2Cl2 and the organic layers were washed thrice with brine and dried over sodium sulfate. The solvents were evaporated in vacuo to obtain the crude products. Some products were purified at this stage. For example, 7-Chloro-2-nitroso-1,2,3,4-tetrahdyroisoquinoline was column chromatographed (3:1 Hexane:Ethylacetate, gradient elution) using combiflash column chromatography. The desired compound was obtained in moderate yields (62%). RRN 777-Chloro-2-nitroso-1, 2, 3, 4-tetrahydroisoquinoline (0166) 1HNMR (CDCl3): delta 3.02-3.13 (m, 2H, -CH2), 4.49-4.53 (m, 2H, -CH2), 4.76 (s, 2H, -CH2), 7.13-7.25 (m, 3H, C1?-C4?-H).

82771-60-6 is used more and more widely, we look forward to future research findings about 7-Chloro-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; Florida A&M University; Redda, Kinfe Ken; Eyunni, Suresh Kumar V. K.; (40 pag.)US2019/100495; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

A common heterocyclic compound, the tetrahydroisoquinoline compound, name is 6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride,cas is 215798-14-4, mainly used in chemical industry, its synthesis route is as follows.

Step B: N-[2-Chloro-6-methyl-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-6-methyphenyl)-3,3-dimethylbutanamide (200 mg, 0.63 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 1.08 (s, 9H), 2.17 (s, 3H), 2.21 (s, 2H), 3.0 (t, J=5.25 Hz, 2H), 3.6 (t, J=5.6 Hz, 2H), 4.5 (s, 2H), 6.9 (s, 1H), 6.95 (s, 1H), 7.3 (m, 1H), 7.5 (m, 2H), 9.13 (s, 1H).

215798-14-4, As the rapid development of chemical substances, we look forward to future research findings about 215798-14-4

Reference£º
Patent; Valeant Pharmaceuticals North America; US2008/139610; (2008); 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: C8H14ClNO276,mainly used in chemical industry, its synthesis route is as follows.,42923-79-5

To a stined solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline (4 g, 22.47 mmol) in DMF (20 mL) was added K2C03 (12.42 g, 89.88 mmol) followed by 2-iodopropane (11.23 mL, 112.35 mmol). The reaction was stined at RT for 6 h. Water (50 mL) was added to the reaction, and the reaction was extracted with EA (2 x 100 mL). The combined organic layers were washed with brine (25 mL), dried (Na2SO4) and concentrated. The crude mixture was purified by column chromatography (Si02, 30% EA/pet. ether) to afford 2-isopropyl-7- nitro-1,2,3,4-tetrahydroisoquinoline (3.2 g, 65%) as a pale yellow liquid. MS (ESI) mlz 221.0 [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; ZENO ROYALTIES & MILESTONES, LLC; HUANG, Peter, Qinhua; BOREN, Brant, Clayton; BUNKER, Kevin, Duane; LIU, Hui; PALIWAL, Sunil; (99 pag.)WO2019/28008; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

22990-19-8, 1-Phenyl-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,22990-19-8

EXAMPLE 13 STR19 2-(Dichloroacetyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline By procedures described in Example 1 (Method A), phenethylamine and benzoyl chloride were converted to 1-phenyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 3.5 g of this isoquinoline compound, 10 ml 10% sodium hydroxide and 50 ml methylene chloride. With this mixture stirred, 1.2 ml dichloroacetyl chloride was added dropwise to the mixture. The mixture was stirred for 10 minutes, then water was added. The organic extract was dried with magnesium sulfate and stripped of solvent. The residue was recrystallized from ethanol to provide 4 g of a white cubic-crystal product having the elemental analysis reported in Table I.

As the paragraph descriping shows that 22990-19-8 is playing an increasingly important role.

Reference£º
Patent; Monsanto Company; US4755218; (1988); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

EXAMPLE 110; Step A; To ice cold concentrated sulfuric acid was added in a dropwise manner 1,2,3,4-tetrahydroisoquinoline (23 mL, 170 mmol), followed by potassium nitrate (18.8 g, 186 mmol) at such a rate that the temperature did not rise above 5 C. After complete addition the mixture was stirred at room temperature for 18 h then poured onto a stirred mixture of ice (700 g) and NH4OH (150 mL). The mixture was extracted with CHCl3 (3¡Á300 mL). The combined CHCl3 layers were washed with saturated NaCl (200 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was dissolved in ethanol (130 mL) and cooled in an ice bath as concentrated hydrochloric acid (22 mL) was added. The formed precipitate was removed by filtration and recrystallized from methanol to give the product (12.45 g, 34%); 1H NMR 500 MHz (DMSO-d6) delta=3.13 (2H, t, J=6.2 Hz), 3.35 (2H, t, J=6.2 Hz), 4.35 (2H, s), 7.50 (1H, d, J=8.5 Hz), 8.07 (1H, dd, J=2.3 and 8.5 Hz), 8.19 (1H, d, J=2.3 Hz) 10.02 (2H, br s).

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

Reference£º
Patent; Butora, Gabor; Goble, Stephen D.; Pastemak, Alexander; Yang, Lihu; Zhou, Changyou; Moyes, Christopher R.; US2008/81803; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

A common heterocyclic compound, the tetrahydroisoquinoline compound, name is Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride,cas is 877861-62-6, mainly used in chemical industry, its synthesis route is as follows.

877861-62-6, Ester 6-17 (250 mg, 1.10 mmol) is combined with N,N-diisopropylethylamine (DIEA) (421 mu, 2.41 mmol) in DCM (10.0 mL) at room temperature, then treated with acetyl chloride (AcCl) (85.9 mu, 1.21 mmol). The resulting mixture is stirred for 1 h, then partitioned between H20 and EtOAc and the phases are separated. The organic phase is washed with IN HCl, saturated aqueous NaHC03, and brine, then dried over Na2S04, filtered, and concentrated to afford 6-18 (258 mg).

As the rapid development of chemical substances, we look forward to future research findings about 877861-62-6

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BRENNEMAN, Jehrod Burnett; HUBER, John D.; RAUDENBUSH, Brian Christopher; SARKO, Christopher Ronald; WO2012/122340; (2012); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

(1 R)-1 -phenyl-1 ,2,3,4-tetrahydroisoquinoline (25 g) recovered from the filtrate of the resolution step, potassium hydroxide (15.5 g), water (12.5 mL), and dimethyl sulfoxide (50 mL) were placed into a clean and dry round bottom flask and stirred for 5 minutes. The reaction mixture was heated to reflux and maintained for 11 hours, 45 minutes. The reaction mass was cooled to 28C and chilled water (375 ml) was added to the reaction mixture and stirred for 35 minutes. The separated solid was then filtered, washed with water (25 mL) and dried at about 55C to afford 13 g of the title compound.

With the complex challenges of chemical substances, we look forward to future research findings about 22990-19-8,belong tetrahydroisoquinoline compound

Reference£º
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; WO2008/128028; (2008); A2;,
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

Into a 20 mL vial was charged 7-nitro-l,2,3,4-tetrahydroisoquinoline, hydrochloric acid salt (0.300 g, 1.398 mmol), methoxyacetyl chloride (0.141 ml, 1.537 mmol), triethylamine (0.429 ml, 3.07 mmol), and dichloromethane (6.99 ml). The reaction was stirred at room temperature for 2 hours. The reaction was diluted with dichloromethane, washed with IN HC1, saturated aqueous sodium bicarbonate, and brine. The organic layer was dried over MgS04, filtered and concentrated to provide the title compound. MS (DCI(+)) m/e 251 (M+H)+.

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; ABBOTT LABORATORIES; BA-MAUNG, Nwe Y.; CLARK, Richard F.; ERICKSON, Scott A.; FIDANZE, Steve D.; KAWAI, Megumi; MANTEI, Robert A.; SHEPPARD, George S.; SORENSON, Bryan K.; WANG, Gary T.; WO2011/53476; (2011); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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 A: Preparation of 2-(6-Bromo-3,4-dihydroisoquinolin-2(lH)-yl)-2-oxoethyl Acetate. To a solution of 6-bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (0.400 g, 1.609 mmol) and triethylamine (1.122 mL, 8.05 mmol) in DCM (10 mL)was added 2-chloro-2- oxoethyl acetate (0.242 g, 1.770 mmol). The reaction was stirred at room temperature for 30 min. The mixture was diluted with DCM, washed with 1 M HCl, brine, dried over Na2SO4, and concentrated to give the title compound without further purification

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.; WO2009/105206; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem