N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate → (S)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate

HRID 2234233Notes

Reaction equation

HRID 2234233 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH:6]([O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH3:3].[C:23]([C@H:26]([C@@H:28]([C:30]([O-:32])=[O:31])[OH:29])[OH:27])([O-:25])=[O:24]>C(O)C>[CH3:1][N:2]([CH2:4][CH2:5][C@H:6]([O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH3:3].[C:23]([C@H:26]([C@@H:28]([C:30]([O-:32])=[O:31])[OH:29])[OH:27])([O-:25])=[O:24]

Participants

3

Reactant 1

HCID 86625060N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate

Product 1

HCID 86625059(S)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(RS)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine-D-tartrate (461 g) is dissolved in ethanol (700 ml) under reflux. After gradual cooling to lab temperature, the mixture is stirred for 164 hours. The precipitated crystals are sucked off and washed with ethanol. The yield is 150 g (32%). Optical purity is 98% ee (CE).

Workup

  1. temperatureunder reflux
  2. temperatureAfter gradual cooling to lab temperature
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-a18cbddc99634ebcb954c8e170fc8326
Source dataset
uspto-grants-2010_05
Patent number
US07709662B2

Reaction notes

Loading…