Water → 3-(Dimethylamino)-1-phenylpropan-1-ol
Reaction equation
[BH4-].[Na+].[CH3:3][N:4]([CH3:15])[CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].O>CC(O)C.CO>[CH3:15][N:4]([CH3:3])[CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Sodium borohydride (6.7 g) was slowly added to a solution of 3-dimethylaminopropiophenone (15.5 g) in 2-propanol (125 ml) and methanol (25 ml). After two hrs, the reaction mixture was stirred with water and extracted with ethyl acetate-ether. The organic extract was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated to give 15.2 g (97%) of 3-dimethylamino-1-phenyl-1-propanol, as an oil. A solution of 3-dimethylamino-1-phenyl-1-propanol (15 g) in dimethylformamide (75 ml) was slowly added to a suspension of sodium hydride (60% oil-dispersion, washed with hexane, 5.5 g) in dimethylformamide (20 ml). A solution of 4-fluorobenzotrifluoride (18 g) in dimethylformamide (20 ml) was added. After two hrs, the reaction mixture was stirred with ice-water and extracted with ether. The ether extract was dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated to provide 27 g (100%) of N,N-dimethyl-3-[ 4-(trifluoromethyl)phenoxy]benzenepropanamine.
Workup
- extractionextracted with ethyl acetate-ether
- extractionThe organic extract
- washwas washed with water and saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe filtrate was evaporated
Sources & evidence
- ORD record
- ord-6fcaed0a1d994b03958c3ee1d0dd477e
- Source dataset
- uspto-grants-1993_07
- Patent number
- US05229417
Reaction notes
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