Ammonium formate → 2,2-Dimethyl-3-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}-1-propanol
Reaction equation
C([O:8][CH2:9][C:10]([CH3:31])([CH3:30])[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[CH2:14][CH2:13]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[CH3:30][C:10]([CH3:31])([CH2:11][N:12]1[CH2:13][CH2:14][N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH2:25][C:26]([F:29])([F:27])[F:28])[CH2:16][CH2:17]1)[CH2:9][OH:8]Participants
Conditions
- Temperature
- 25 °C
Procedure
A mixture of 3-benzyloxy-2,2-dimethyl-1-(4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl)propane (2.5 g, 6 mol), 10% palladium on carbon (2.8 g), ammonium formate (3.8 g, 59.6 mmol) and methanol (130 mL) was heated 1 hour at reflux. The reaction mixture was allowed to cool to approximately 25° C., then filtered over celite (washing through with methanol and saturated sodium carbonate (20 mL)) and concentrated. The residue was dissolved in water and the solution was extracted with methylene chloride (3×20 mL). The combined extracts were dried (MgSO4) and concentrated. The residue was purified by chromatography on silica gel eluting with hexanes/ethyl acetate (8:2) to give 2,2-dimethyl-3-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}-1-propanol (1.6 g, 5.1 mol).
Workup
- temperaturewas heated 1 hour
- temperatureat reflux
- filtrationfiltered over celite (washing through with methanol and saturated sodium carbonate (20 mL))
- concentrationconcentrated
- dissolutionThe residue was dissolved in water
- extractionthe solution was extracted with methylene chloride (3×20 mL)
- dry with materialThe combined extracts were dried (MgSO4)
- concentrationconcentrated
- customThe residue was purified by chromatography on silica gel eluting with hexanes/ethyl acetate (8:2)
Sources & evidence
- ORD record
- ord-304f1da09ac647be923d2857aa3cbf46
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05859014
Reaction notes
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