2-(1,2,3,4-Tetrahydroisoquinolin-3-yl)ethan-1-ol → (RS)-3-(2-Hydroxyethyl)-N-(3-methylisoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide

HRID 1449133Notes

Reaction equation

[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([CH3:14])[N:8]=[CH:9]2)=[C:2]=[S:3].[OH:15][CH2:16][CH2:17][CH:18]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][NH:19]1>C(O)C>[OH:15][CH2:16][CH2:17][CH:18]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][N:19]1[C:2](=[S:3])[NH:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([CH3:14])[N:8]=[CH:9]2

Participants

Conditions

Temperature: 20 °C

Procedure

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.

Workup

customthe mixture is evaporated to dryness at 40° C. under reduced pressure (30 mm Hg)

Sources & evidence

ORD record: ord-72f2e82c090f422ca576cc23921a7af2
Source dataset: uspto-grants-1980_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04189480

Reaction notes

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