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

HRID 1449134Notes

Reaction equation

HRID 1449134 reaction equation
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([CH2:14][CH2:15][CH3:16])[N:8]=[CH:9]2)=[C:2]=[S:3].[OH:17][CH2:18][CH2:19][CH:20]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][NH:21]1>C(O)C>[OH:17][CH2:18][CH2:19][CH:20]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][N:21]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]([CH2:14][CH2:15][CH3:16])[N:8]=[CH:9]2

Participants

4

Reactant 2

HCID 128748552-(1,2,3,4-Tetrahydroisoquinolin-3-yl)ethan-1-olHCID 203500705-Isothiocyanato-3-propylisoquinoline

Product 1

HCID 20350063(RS)-3-(2-Hydroxyethyl)-N-(3-propylisoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamideYield 71.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

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.

Workup

  1. filtrationthe crystals which have appeared are filtered off
  2. washwashed with ethanol (2×2 cc)

Sources & evidence

ORD record
ord-5019c18158094db3b96db829c7007a82
Source dataset
uspto-grants-1980_02
Patent number
US04189480

Reaction notes

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