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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 1449133
Notes
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Reaction equation

HRID 1449133 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 128748552-(1,2,3,4-Tetrahydroisoquinolin-3-yl)ethan-1-olHCID 130143215-Isothiocyanato-3-methylisoquinoline

Product 1

HCID 20350066(RS)-3-(2-Hydroxyethyl)-N-(3-methylisoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamideYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes