(RS)-6-hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine → (RS)-6-Hydroxymethyl-5-[(3-methylisoquinol-5-yl)thiocarbamoyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

HRID 443840Notes

Reaction equation

HRID 443840 reaction equation
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([CH3:14])[N:8]=[CH:9]2)=[C:2]=[S:3].[OH:15][CH2:16][CH:17]1[NH:22][CH2:21][C:20]2[CH:23]=[CH:24][S:25][C:19]=2[CH2:18]1>C(O)C>[OH:15][CH2:16][CH:17]1[N:22]([C:2](=[S:3])[NH:1][C:4]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:5]=2[CH:6]=[C:7]([CH3:14])[N:8]=[CH:9]3)[CH2:21][C:20]2[CH:23]=[CH:24][S:25][C:19]=2[CH2:18]1

Participants

4

Reactant 2

HCID 12939919(RS)-6-hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridineHCID 130143215-Isothiocyanato-3-methylisoquinoline

Product 1

HCID 23465914(RS)-6-Hydroxymethyl-5-[(3-methylisoquinol-5-yl)thiocarbamoyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridineYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Isothiocyanato-3-methylisoquinoline (5.1 g) is added to a solution of (RS)-6-hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (3.4 g) in absolute ethanol (55 cc). After 15 hours at a temperature of about 20° C., the resulting crystals are filtered off, washed with diisopropyl ether and then dried at 60° C. under reduced pressure (0.1 mm Hg; 0.013 kPa). (RS)-6-Hydroxymethyl-5-[(3-methylisoquinol-5-yl)thiocarbamoyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (6.9 g), melting at 190° C., is thus obtained.

Workup

  1. filtrationthe resulting crystals are filtered off
  2. washwashed with diisopropyl ether
  3. customdried at 60° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)

Sources & evidence

ORD record
ord-8f6d3b4a2eb14a2db17b0708d644a402
Source dataset
uspto-grants-1981_04
Patent number
US04261999

Reaction notes

Loading…