Ammonia → N,N-Dimethyl-3-((naphthalen-1-yl)oxy)-3-(thiophen-2-yl)propan-1-amine
Reaction equation
C(O)(=O)C(O)=O.[CH3:7][N:8]([CH3:28])[CH2:9][CH2:10][CH:11]([O:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1.N>O.C1CCCCC1>[CH3:28][N:8]([CH3:7])[CH2:9][CH2:10][CH:11]([O:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
(R,S)—N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine oxalate salt (5, HA=oxalic acid) (255 gm) was suspended in a mixture of water (1275 ml) and cyclohexane (765 ml). This suspension was basified with aqueous ammonia solution (pH 12.5-13.5). Organic layer was separated, washed with water and concentrated under reduced pressure to give oily mass of racemic condensed compound, (R,S)—N.N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propanamine (6a+6b) (195 gm). The oily mass was dissolved in 2000 ml of mixture of methanol (5%) and ethyl acetate (95%). To this clear solution 1.0 mole equivalent of di-benzoyl-(L)-tartaric acid monohydrate (236.4 gm) was added. The clear solution was stirred for half an hour and seeded with crystals of (S)—N,N-dimethyl-3-(1-naphthylenyloxy)-3-(2-thienyl)propanamine dibenzoyl-(L)-tartarate salt (8a). The solution was stirred for 12-15 hours at 25-30° C. to get white thick slurry. The solid obtained was filtered, washed with ethanol (255 ml) and dried under reduced pressure.
Workup
- customOrganic layer was separated
- washwashed with water
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d194d5c679b64902a9e995f5b8e5ac2d
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08269023B2
Reaction notes
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