Category: tetrahydroisoquinoline

91-21-4, 1,2,3,4-Tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(a) 1,2,3,4-Tetrahydroisoquinoline (50 g, 0.376M) was dissolved in concentrated H2 SO4 (180 ml) with cooling. Solid potassium nitrate (40.4 g, 0.4M) was added in portions, keeping the temperature below 5¡ã C., over 4 hours. The reaction mixture was allowed to stand overnight at room temperature and was then poured onto ice, basified with NH4 OH and was then extracted with CHCl3. After evaporation, the residue was dissolved in ethanol and concentrated HCl was added. The resulting precipitated hydrochloride salt was filtered off and recrystallized from methanol to yield 7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride (31.5 g, 39percent), m.p. 268¡ã-269¡ã C.

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

Reference£º
Patent; SmithKline & French Laboratories, Ltd.; US4812573; (1989); A;,
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.151838-62-9,2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid,as a common compound, the synthetic route is as follows.

To solution of 1- (2-allyl-4-benzyloxy-pyrrolidin-I-yi)-2-amino-3- (4-fluorophenyl)-propan-I-one, 54, (1.4 mmol) is dissolved in DMF (10 mL) are added N-Boc-tetrahydroisoquinoline-3-carboxylic acid (0.47g, 1.5 mmol), 1-hydroxybenzotriazole (0.43g, 2.8 mmol), N-methylmorpholine (0.84g, 8.3 mmol) and 1- (3-dimethylamino-propyl)-3-ethylcarbodiimide (0.32g, 1.7 mmol) at 0 C. The reaction mixture is stirred at 0 C for 1 hour and then warmed to room temperature and stirred an additional 1.5 hour. The reaction is quenched with saturated NH4CI solution and then extracted 3 times with EtOAc (70 mL). The organic layers are combined, washed with saturated NaCI solution, dried over Na2SO4, and the solvent is removed in vacuo. The crude product is purified over silica to afford 0.69 g (77% yield) of the desired product as a white solid.’H NMR (300 MHz, MeOD, Rotamers) 5 6.90-7. 41 (m, 13H), 5.55-5. 81 (m, 1 H), 4.32-5. 12 (m, 8H), 3.94-4. 18 (m, 2H), 2.75-3. 89 (m, 6H), 2.39-2. 64 (m, 1 H), 1.78-2. 29 (m, 2H), 1.20-1. 64 (m, 10H) ; MS (ESMS) m/z 642.2 (M+H) +.

The synthetic route of 151838-62-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; THE PROCTER & GAMBLE COMPANY; WO2004/37797; (2004); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

166591-85-1, 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

T3P (50% in EtOAc) (3.22 mL, 5.41 mmol) was added to a solution of 2-(/eri- butoxycarbonyl)-l,2,3,4-tetrahydroisoquinoline-l-carboxylic acid (1.00 g, 3.61 mmol),(trans)- l-methoxy-2,3-dihydro-1H-inden-2-amine (Intermediate 2, 0.647 g, 3.97 mmol) and TEA (0.754 mL, 5.41 mmol) in DCM (20 mL). The reaction was stirred at room temperature for 1.5 h. The mixture was partitioned between DCM and saturated NaHCCh, dried (phase separator) and concentrated in vacuo. The crude product was purified by column chromatography on silica, eluted with 0-50% EtOAc/petroleum ether to afford the title compound. ‘Eta NMR (300 MHz, DMSO-4s) delta ppm 1.34 – 1.50 (m, 9 H), 2.66 – 2.83 (m, 2 H), 2.94 – 3.09 (m, 1 H), 3.13 – 3.28 (m, 3 H), 3.34 – 3.39 (m, 1 H), 3.45 – 3.66 (m, 1 H), 3.82 – 3.96 (m, 1 H), 4.20 – 4.37 (m, 1 H), 4.60 – 4.74 (m, 1 H), 5.17 – 5.41 (m, 1 H), 7.13 – 7.37 (m, 7 H), 7.40 – 7.59 (m, 1 H), 8.57 – 8.80 (m, 1 H) (0622) MS ES+: 445 (M+Na)

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Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; LIWICKI, Gemma; MACK, Stephen; STEPHENSON, Anne; TEALL, Martin; WHITE, Kathryn; (168 pag.)WO2018/47983; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

99365-69-2, 7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1) Production of 2-(7-nitro-3,4-dihydroisoquinolin-2(1H)-yl)ethanol: An acetonitrile solution (30 mL) of 3 g of the compound obtained in Production Example 22-1), 2.3 g of 2-chloroethanol and 3.9 g of potassium carbonate was stirred at 100¡ãC for 15 hours. The reaction liquid was cooled, diluted with chloroform and washed with saturated saline water. The organic layer was washed with saturated saline water, dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting crude product was purified through basic silica gel column chromatography (hexane/ethyl acetate) and further through silica gel column chromatography (hexane/ethyl acetate) to obtain 1.5 g of the entitled compound as a colorless solid. 1H-NMR (CDCl3) delta: 8.00 (1H, dd, J=8.5, 2.2 Hz), 7.93 (1H, d, J=2.2 Hz), 7.28-7.25 (1H, m), 3.78 (2H, s), 3.74 (2H, t, J=5.5 Hz), 3.00 (2H, t, J=5.9 Hz), 2.86 (2H, t, J=5.9 Hz), 2.76 (2H, t, J=5.5 Hz) ESI-MS Found: m/z [M+H] 223

As the paragraph descriping shows that 99365-69-2 is playing an increasingly important role.

Reference£º
Patent; Banyu Pharmaceutical Co., Ltd.; EP2168966; (2010); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

57196-62-0, 6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (2. 0g,10mmol)And triethylamine (3.038, 30 mmol) were dissolved in dichloromethane (100 mL) Acetic anhydride (1.53 g, 15 mmol) was added and reacted at room temperature for 2 hours. Water (50 mL) was added and the aqueous phase was extracted with dichloromethane (50 mL X). The organic phases were combined, Washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude product (2.2 g).

The synthetic route of 57196-62-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wu Yongqian; (29 pag.)CN104876914; (2017); B;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

91-21-4, 1,2,3,4-Tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a mortar 2 g of P2O5/silica gel (65% w/w)1 (10 mmol) and 1,2,3,4-tetrahydroisoquinoline (10 mmol, 1.33 g) was triturated for 30 s, and then 5 ml of HNO3 65% was added drop-wise and the mixture was further triturated with a pestle at room temperature for 20 min until a deep-yellow color appeared, at which point TLC (n-hexane:EtOAc 70:30) showed complete disappearance of 1,2,3,4-tetrahydroisoquinoline (30 min). To the reaction mixture was added diethyl ether (50 ml) and the solid was separated through a short pad of silica gel and washed with diethyl ether (2 ¡Á 15 ml). The filtrate was washed with NaHCO3 10% (20 ml) and dried (MgSO4). The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (n-Hexane:EtOAc, 2:1), 7-nitro-1,2,3,4-tetrahydroisoquinoline (2b) was obtained (8 mmol, 1.4 g 80%) as a yellow solid, mp 121 C. 1H NMR, delta: 8.05 (m, 2H), 7.60 (m, 1H,), 3.82 (s, 2H), 3.38 (t, 2H, J = 7.4 Hz), 3.12 (t, 2H, J = 7.4 Hz), 2.83 (s, 1H). 13C NMR, delta: 150.6, 145.0, 140.3, 129.6, 122.6, 121.4, 46.9, 44.1, 28.1. EMS [M+H+] for C9H10N2O2, Calcd 179.0740. Found, 179.1121.

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

Reference£º
Article; Hajipour, Abdol R.; Guo, Lian-Wang; Pal, Arindam; Mavlyutov, Timur; Ruoho, Arnold E.; Bioorganic and Medicinal Chemistry; vol. 19; 24; (2011); p. 7435 – 7440;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

215798-14-4, 6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step B: [2,6-Dimethyl-4-(6-trifluoromethyl-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-carbamic acid ethyl ester Bis(dibenzylidineacetone)palladium (17 mg, 0.03 mmol) and (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethylamine (35 mg, 0.09 mmol) were added to dry toluene (5 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (166 mg, 1.48 mmol), 6-Trifluoromethyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride salt (176 mg, 0.74 mmol) and (4-Bromo-2,6-dimethyl-phenyl)-carbamic acid ethyl ester (200 mg, 0.74 mmol) were then added and the reaction mixture was stirred at 80 C. overnight. The reaction mixture was then cooled to room temperature filtered through silica gel and purified by preparative thin layer chromatography (DCM 100%) to give the desired compound as a solid.1H NMR (DMSO-d6, 400 MHz) delta 1.23 (t, J=7.2 Hz, 3H), 2.12 (s, 6H), 3.0 (t, J=6.4 Hz, 2H), 3.52 (t, J=6.3 Hz, 2H), 4.08 (q, J=13.6, 8.3 Hz, 2H), 4.42 (s, 2H) 6.73 (s, 2H), 7.46 (d, J=7.4, 1H), 7.54 (m, 2H), 8.32 (s, 1H).

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

42923-77-3, 6-Methoxy-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

D. 6-Hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester A solution of 8.00 g (49 mmol) of 6-Methoxy-1,2,3,4-tetrahydro-isoquinoline in 196 mL of 48% hydrobromic acid was refluxed for 3 h. The mixture was then concentrated and coevaporated several times with ethanol. The resulting slurry was filtered and dried under vacuum to give 7.43 g of 1,2,3,4-Tetrahydro-isoquinolin-6-ol hydrobromide as a solid.

As the paragraph descriping shows that 42923-77-3 is playing an increasingly important role.

Reference£º
Patent; Pfizer Inc; US5936089; (1999); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

91-21-4, 1,2,3,4-Tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 Conc. sulfuric acid (80 ml) was added by small portions to tetrahydroisoquinoline (24.4 g, 183 mmol) under ice-cooling for dissolution. Then, 60percent nitric acid (18 ml) was added dropwise from a funnel and the mixture was stirred under ice-cooling for 3 hr. The mixture was stirred at room temperature for 18 hr. The reaction mixture was diluted with water under ice-cooling, and 35percent aqueous sodium hydroxide solution was added to adjust the solution to pH 12. After extraction with chloroform, the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in ethanol (180 ml) and conc. hydrochloric acid (20 ml) was added under ice-cooling. The precipitated brown crystals were collected by filtration with suction to give 7-nitrotetrahydroisoquinoline hydrochloride (7.18 g, 22percent).

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

Reference£º
Patent; Japan Tobacco Inc.; US6410561; (2002); B1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

57060-88-5, Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of Boc-Dmt-OH (309 mg, 1 mmol), HBTU (379 mg, 1 mmol) and DIEA (348 muL, 2 mmol) in 5 mL DMF was added a solution of HCl x H-Tic-OMe (227.5 mg, 1 mmol) and DIEA (174 muL, 1 mmol) in 5 mL DMF. The reaction mixture was stirred for 5 h at room temperature and progress of the reaction was monitored by TLC. After solvent evaporation in vacuo, the residue was dissolved in 50 mL AcOEt and the resulting solution was washed with 5% KHSO4 (aq.), saturated NaHCO3 (aq.) and brine. The organic phase was dried (MgSO4), filtered and evaporated to dryness, yielding 430 mg of crude product (90% yield). The crude Boc-protected dipeptide ester was deprotected by treatment with aqueous TFA (95% vv) for 45 min under stirring and cooling with ice. After TFA evaporation in vacuo, the TFA salt of the dipeptide ester was precipitated with ether (Et2O), affording 300 mg (90% yield) of crude product which was purified by preparative HPLC. TFA x H-Dmt-Tic-OMe: TLC Rf (I) 0.55; MS [M+H]+ 383.

57060-88-5 Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride 12248067, atetrahydroisoquinoline compound, is more and more widely used in various.

Reference£º
Article; Weltrowska, Grazyna; Nguyen, Thi M.-D.; Chung, Nga N.; Wilkes, Brian C.; Schiller, Peter W.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 18; (2013); p. 5082 – 5085;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem