Sodium Hydroxide → N-methyl-3-[[4-(trifluoromethyl)phenyl]thio]benzenepropanamine
Reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9](Cl)[CH:8]=1.[OH-].[Na+].[F:16][C:17]([F:26])([F:25])[C:18]1[CH:23]=[CH:22][C:21]([SH:24])=[CH:20][CH:19]=1>>[CH3:2][NH:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:24][C:21]2[CH:20]=[CH:19][C:18]([C:17]([F:16])([F:25])[F:26])=[CH:23][CH:22]=2)[CH:8]=1Participants
Procedure
N-Methyl-3-chloro-benzenepropanamine hydrochloride (13.14 g, 0.06 mol), 25%, by weight, sodium hydroxide solution (9.6 g of solution; 0.06 mol of sodium hydroxide), sodium hydroxide pellets (2.0 g, 0.05 mol and 4-trifluoromethylbenzenethiol (8.3 g, 0.05 mol) were reacted to provide N-methyl-3-[[4-(trifluoromethyl)phenyl]thio]benzenepropanamine as an oil. The oil was dissolved in 200 ml diethyl ether and hydrochloric acid gas was passed through the solution for about 15 minutes. The solvent was removed under reduced pressure to provide an oil which was dissolved in a 1:1:1 ethyl acetate:diethyl ether:hexane solvent mixture. The solvents were slowly removed under reduced pressure and crystals precipitated. The crystals were purified by preparing a slurry of the crystals partially dissolved in a 1:1:1 methylene chloride:ethyl acetate:diethyl ether solvent system. The mixture was chilled to 0° C. and the solids were recovered by filtration to provide 13.0 g of title compound. m.p. =125°-130° C.
Sources & evidence
- ORD record
- ord-1887954d9c534f19a0380bef549b0210
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04902710
Reaction notes
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