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

HRID 656689Notes

Reaction equation

HRID 656689 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(OCC)C>C1COCC1.O>[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

5

Reactant 2

HCID 3283Diethyl EtherHCID 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 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(RS)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine/D-tartrate (773 g, 1 mole) is dissolved in THF (1500 ml) with an addition of water (40 ml) under reflux. After gradual cooling down to ambient temperature, diethylether (300 ml) is added drop-wise to the mixture over 6 hours. The precipitated crystals are sucked off and washed with THF. Yield: 232 g (30%). Optical purity: 93% ee (CE).

Workup

  1. temperatureunder reflux
  2. washwashed with THF

Sources & evidence

ORD record
ord-ff559a1ba32e45709c5aa706542e7b43
Source dataset
uspto-grants-2011_12
Patent number
US08071791B2

Reaction notes

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