Isopropanol → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(1-hydroxyethyl)-4-phenylpiperidine hydrochloride
Reaction equation
CC(O)C.[ClH:5].[C:6]([C:9]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]2[C:22]3[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=3[O:20][N:19]=2)[CH2:11][CH2:10]1)(=[O:8])[CH3:7].[BH4-].[Na+]>CO>[ClH:5].[F:27][C:25]1[CH:24]=[CH:23][C:22]2[C:18]([CH2:17][CH2:16][CH2:15][N:12]3[CH2:11][CH2:10][C:9]([CH:6]([OH:8])[CH3:7])([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:14][CH2:13]3)=[N:19][O:20][C:21]=2[CH:26]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 50 ml of 2-propanol and 10 ml of methanol, was added 2.8 g of 4-acetyl-1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)-propyl]-4-phenylpiperidine hydrochloride and 0.76 g of sodium borohydride. After stirring at ambient temperature for twenty hrs, the mixture was evaporated. The residue was stirred with 100 ml of water for ten mins and then extracted with ether. The ether extract was washed with water (2x), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the ether solution was acidified to pH 1 with ethereal hydrogen chloride. The resultant precipitate was collected and dried to give 2.3 g (78%) of product, mp 80° C. Recrystallization from ethyl acetate/methanol (9:1) gave the analytical sample, mp 143°-147° C.
Workup
- customthe mixture was evaporated
- stirringThe residue was stirred with 100 ml of water for ten mins
- extractionextracted with ether
- extractionThe ether extract
- washwas washed with water (2x), saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationAfter filtering
- customThe resultant precipitate was collected
- customdried
Sources & evidence
- ORD record
- ord-7bee0eaddddc40e0b6eeb34002eaebf0
- Source dataset
- uspto-grants-1986_05
- Patent number
- US04591586
Reaction notes
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