2-(1,2,3,4-tetrahydroisoquinolin-3-yl)ethanol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5-Isothiocyanato-3-methoxymethylisoquinoline (18.2 g) is added to a solution of (RS)-3-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline (14 g) in ethanol (250 cc). The mixture is stirred for 24 hours at a temperature of about 20° C. The precipitate formed is filtered off and washed with ethanol (2×10 cc) and diethyl ether (2×10 cc). (RS)-3-(2-Hydroxyethyl)-N-(3-methoxymethylisoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide (20.9 g), m.p. 152° C., is thus obtained. The precipitate formed is filtered off washed with ethanol (2×10 cc) and diethyl ether (2×10 cc)

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5-Isothiocyanato-3-methoxymethylisoquinoline (18.2 g) is added to a solution of (RS)-3-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline (14 g) in ethanol (250 cc). The mixture is stirred for 24 hours at a temperature of about 20° C. The precipitate formed is filtered off and washed with ethanol (2×10 cc) and diethyl ether (2×10 cc). (RS)-3-(2-Hydroxyethyl)-N-(3-methoxymethylisoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide (20.9 g), m.p. 152° C., is thus obtained. The precipitate formed is filtered off washed with ethanol (2×10 cc) and diethyl ether (2×10 cc)

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5-Isothiocyanato-3-propylisoquinoline (4.5 g) is added to a solution of (RS)-3-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline (3.5 g) in absolute ethanol (35 cc). After stirring for 20 hours at a temperature of about 20° C., the crystals which have appeared are filtered off and then washed with ethanol (2×2 cc). (RS)-3-(2-Hydroxyethyl)-N-(3-propylisoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide (5.7 g) is thus obtained; after recrystallisation from propanol (50 cc), it melts at 175° C. the crystals which have appeared are filtered off washed with ethanol (2×2 cc)

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5-Isothiocyanato-3-methylisoquinoline (8.8 g) is added to a solution of (RS)-3-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline (7.8 g) in ethanol (150 cc). A white precipitate rapidly forms. After stirring for 17 hours at a temperature of about 20° C., the mixture is evaporated to dryness at 40° C. under reduced pressure (30 mm Hg). (RS)-3-(2-Hydroxyethyl)-N-(3-methylisoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide (16.5 g) is thus obtained in the form of pale yellow crystals. the mixture is evaporated to dryness at 40° C. under reduced pressure (30 mm Hg)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3-Isothiocyanatopyridine (2.6 g) is added to a solution of (RS)-3-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline (3.3 g) in ethanol (40 cc). A white precipitate forms after 5 hours; stirring is continued for 12 hours at a temperature of about 20° C. The crystals which have appeared are filtered off and washed with diethyl ether (2×5 cc). (RS)-3-(2-Hydroxyethyl)-N-(pyrid-3-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide (4.7 g), melting at 174° C., is thus obtained. is continued for 12 hours at a temperature of about 20° C The crystals which have appeared are filtered off washed with diethyl ether (2×5 cc)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (+)-2-(2-Benzyl-1,2,3,4-tetrahydro-isoquinolin-3-yl)-ethanol (610 mg, 2.3 mmol) was hydrogenated at 40 p.s.i.g. on a Parr Apparatus (305 mg of 10% palladium-on-carbon catalyst; methanol/concentrated hydrochloric acid solvent (15 ml and 0.25 ml, respectively) for 5 hours. The catalyst was filtered, and the filtrate was concentrated in vacuo to an oil, which was dissolved in dilute aqueous (pH 9) sodium carbonate/methylene chloride (50 ml of each). The aqueous phase was separated and extracted with two 10 ml portions of methylene chloride. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to afford the title compound as a viscous colorless oil (quantitative yield). The catalyst was filtered the filtrate was concentrated in vacuo to an oil, which was dissolved in dilute aqueous (pH 9) sodium carbonate/methylene chloride (50 ml of each) The aqueous phase was separated extracted with two 10 ml portions of methylene chloride The combined organic extracts were dried over anhydrous sodium sulfate concentrated in vacuo

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5-Isothiocyanato-3-methoxymethylisoquinoline (18.2 g) is added to a solution of (RS)-3-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline (14 g) in ethanol (250 cc). The mixture is stirred for 24 hours at a temperature of about 20° C. The precipitate formed is filtered off and washed with ethanol (2×10 cc) and diethyl ether (2×10 cc). (RS)-3-(2-Hydroxyethyl)-N-(3-methoxymethylisoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide (20.9 g), m.p. 152° C., is thus obtained. The precipitate formed is filtered off washed with ethanol (2×10 cc) and diethyl ether (2×10 cc)