5-Isothiocyanato-3-methoxymethylisoquinoline → (RS)-3-(2-Hydroxyethyl)-N-(3-methoxymethylisoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide

HRID 443813Notes

Reaction equation

HRID 443813 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][O: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][O:15][CH3:16])[N:8]=[CH:9]2

Participants

4

Reactant 2

HCID 128748545-Isothiocyanato-3-methoxymethylisoquinolineHCID 128748552-(1,2,3,4-Tetrahydroisoquinolin-3-yl)ethan-1-ol

Product 1

HCID 12874856(RS)-3-(2-Hydroxyethyl)-N-(3-methoxymethylisoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamideYield 64.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

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.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. washwashed with ethanol (2×10 cc) and diethyl ether (2×10 cc)

Sources & evidence

ORD record
ord-3e32b9599e124c32b06419d98519dd9d
Source dataset
uspto-grants-1981_04
Patent number
US04261992

Reaction notes

Loading…