[(3S)-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol → HCID 54416793, compound

HRID 461803Notes

Reaction equation

HRID 461803 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][C@@H:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][NH:13]1>C(O)C>[OH:10][CH2:11][C@@H:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][N:13]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 776757[(3S)-1,2,3,4-tetrahydroisoquinolin-3-yl]methanolHCID 27372423-Pyridyl isothiocyanate

Product 1

HCID 54416793HCID 54416793, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Isothiocyanatopyridine (6.8 g.) is added to a solution of (S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline (8.15 g.) in ethanol (150 cc.). After 3 hours at a temperature of about 20° C., the solution is cooled to 0° C. The white crystals which have appeared are filtered off and are then recrystallised from propanol (200 cc.). After filtration, the crystals are washed with propanol (2 × 10 cc.) and then dried at 60° C. under reduced pressure (1 mm. Hg). (S)-3-Hydroxymethyl-N-(pyrid-3-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide (12.1 g.) melting at 192° C is thus obtained.

Workup

  1. filtrationThe white crystals which have appeared are filtered off
  2. customare then recrystallised from propanol (200 cc.)
  3. filtrationAfter filtration
  4. washthe crystals are washed with propanol (2 × 10 cc.)
  5. customdried at 60° C. under reduced pressure (1 mm. Hg)

Sources & evidence

ORD record
ord-94f46c448f7948bd976d63deb9fc92e1
Source dataset
uspto-grants-1977_12
Patent number
US04064247

Reaction notes

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