Water → cis-4-[[3,5-Bis(trifluoromethyl)benzyl]oxy]-N-methyl-3-phenyl-1-piperidinecarboxamide

HRID 1437633Notes

Reaction equation

HRID 1437633 reaction equation
Cl.[F:2][C:3]([F:29])([F:28])[C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C[CH2:31][N:32]([CH2:35]C)CC.[OH2:37]>C(#N)C.CN=C=O>[F:29][C:3]([F:2])([F:28])[C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:23]=1)[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:31]([NH:32][CH3:35])=[O:37])[CH2:11][C@H:10]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 86606807cis-4-[[3,5-Bis(trifluoromethyl)benzyl]oxy]-3-phenylpiperidine hydrochloride

Product 1

HCID 86606812cis-4-[[3,5-Bis(trifluoromethyl)benzyl]oxy]-N-methyl-3-phenyl-1-piperidinecarboxamideYield 95%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 12228Methyl IsocyanateSolvent

Procedure

To a solution of the compound (0.20 g) obtained in Example 1 and Et3N (0.19 ml) in acetonitrile (5 ml), methyl isocyanate (0.050 ml) was added, and the reaction mixture was stirred at room temperature for 14 hours. The reaction mixture was poured into water, and then the product was. extracted with ethyl acetate. The organic layer was washed with an aqueous 10% citric acid solution and saturated brine, dried, and then the solvent was evaporated under reduced pressure. The obtained residue was isolated and purified by silica gel column chromatography (ethyl acetate:methanol=20:1) to obtain the title compound as colorless oil (0.20 g, 95%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous 10% citric acid solution and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was isolated
  6. custompurified by silica gel column chromatography (ethyl acetate:methanol=20:1)

Sources & evidence

ORD record
ord-41de082fff154dba95b4e758b7672e67
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

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