3-Pyridyl isothiocyanate → (RS)-3-(2-Hydroxyethyl)-N-(pyrid-3-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide

HRID 1449132Notes

Reaction equation

HRID 1449132 reaction equation
[N:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)=[C:2]=[S:3].[OH:10][CH2:11][CH2:12][CH:13]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][NH:14]1>C(O)C>[OH:10][CH2:11][CH2:12][CH:13]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][N:14]1[C:2](=[S:3])[NH:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 27372423-Pyridyl isothiocyanateHCID 128748552-(1,2,3,4-Tetrahydroisoquinolin-3-yl)ethan-1-ol

Product 1

HCID 20350069(RS)-3-(2-Hydroxyethyl)-N-(pyrid-3-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamideYield 80.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Isothiocyanatopyridine (2.6 g) is added to a solution of (RS)-3-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline (3.3 g) in ethanol (40 cc). A white precipitate forms after 5 hours; stirring is continued for 12 hours at a temperature of about 20° C. The crystals which have appeared are filtered off and washed with diethyl ether (2×5 cc). (RS)-3-(2-Hydroxyethyl)-N-(pyrid-3-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide (4.7 g), melting at 174° C., is thus obtained.

Workup

  1. waitis continued for 12 hours at a temperature of about 20° C
  2. filtrationThe crystals which have appeared are filtered off
  3. washwashed with diethyl ether (2×5 cc)

Sources & evidence

ORD record
ord-e9071baa09e9415f8a287d553d3ea20a
Source dataset
uspto-grants-1980_02
Patent number
US04189480

Reaction notes

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