[(3S)-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol → (S)-3-Hydroxymethyl-N-(isoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide

HRID 461804Notes

Reaction equation

HRID 461804 reaction equation
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2)=[C:2]=[S:3].[OH:14][CH2:15][C@@H:16]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][NH:17]1>C(O)C>[OH:14][CH2:15][C@@H:16]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][N:17]1[C:2](=[S:3])[NH:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2

Participants

4

Reactant 2

HCID 776757[(3S)-1,2,3,4-tetrahydroisoquinolin-3-yl]methanolHCID 130143205-Isothiocyanatoisoquinoline

Product 1

HCID 54449916(S)-3-Hydroxymethyl-N-(isoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamideYield 74.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Isothiocyanatoisoquinoline (0.93 g.) is added to a solution of (S)-3-hydroxymethyl-1,2,3,4-tetrahydro isoquinoline (0.82 g.) in ethanol (10 cc.). After 15 hours at a temperature of about 20° C., the crystals formed are filtered off, washed with ethanol and then dried at 60° C. under reduced pressure (0.1 mm. Hg). (S)-3-Hydroxymethyl-N-(isoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide (1.3 g. ), melting at 190° C., is thus obtained.

Workup

  1. customthe crystals formed
  2. filtrationare filtered off
  3. washwashed with ethanol
  4. customdried at 60° C. under reduced pressure (0.1 mm. Hg)

Sources & evidence

ORD record
ord-52e0171158014d8ead1cb0daa4b2bb11
Source dataset
uspto-grants-1977_12
Patent number
US04064247

Reaction notes

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