3-((3,5-Bis(trifluoromethyl)phenyl)methyloxy)-2-phenylpiperidine → HCID 44307089, compound
Reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][C@H:15]2[CH2:20][CH2:19][CH2:18][NH:17][C@H:16]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl.FC(F)(F)C1C=[C:34]([CH2:42][O:43][C@H]2CCCN[C@H]2C2C=CC=CC=2)C=C(C(F)(F)F)C=1>>[C:42]([N:17]1[CH2:18][CH2:19][CH2:20][C@H:15]([O:14][CH2:13][C:5]2[CH:4]=[C:3]([C:2]([F:27])([F:1])[F:28])[CH:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:6]=2)[C@@H:16]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:43])[CH3:34]Participants
3
Conditions
- Temperature
- 23 °C
Procedure
To a solution of (+)-cis-3-((3,5-bis(trifluoromethyl) phenyl)methyloxy)-2-phenyl piperidine prepared from hydrochloride salt (Example 5, 1.0 g) by partitioning between aqueous sodium carbonate and dichloromethane) in dry dichloromethane (5 ml) was added pyridine (0.67 ml), acetic anhydride (0.79 ml) and 4,4-dimethylamine pyridine (10 mg). After the solution had been stirred for 3 h at 23° C., saturated sodium bicarbonate solution was added and the organic phase dried (MgSO4), evaporated in vacuo and chromatographed on silica gel to give the title compound as an oil. Found: C, 59.51; H, 4.90; N, 3.09. Calcd for C22H21NO2F6 ; C, 59.33; H, 4.75; N, 3.14%.
Workup
- customby partitioning between aqueous sodium carbonate and dichloromethane) in dry dichloromethane (5 ml)
- additionwas added pyridine (0.67 ml), acetic anhydride (0.79 ml) and 4,4-dimethylamine pyridine (10 mg)
- additionsaturated sodium bicarbonate solution was added
- dry with materialthe organic phase dried (MgSO4)
- customevaporated in vacuo
- customchromatographed on silica gel
Sources & evidence
- ORD record
- ord-b5125227cb6b42c390b4cd4801e254a9
- Source dataset
- uspto-grants-1995_10
- Patent number
- US05459270
Reaction notes
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