Trifluoroacetic acid → 4-(4-fluorophenyl)-N-[(1S)-1-(4-fluorophenyl)ethyl]piperidine-4-carboxamide;2,2,2-trifluoroacetic acid

HRID 2189970Notes

Reaction equation

HRID 2189970 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)([C:14](=[O:25])[NH:15][C@H:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH3:17])[CH2:10][CH2:9]1)=O)(C)(C)C.[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>ClCCl>[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36].[F:24][C:21]1[CH:22]=[CH:23][C:18]([C@@H:16]([NH:15][C:14]([C:11]2([C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:25])[CH3:17])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 666711954-(4-fluoro-phenyl)-4-[(S)-1-(4-fluoro-phenyl)-ethylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866462374-(4-fluorophenyl)-N-[(1S)-1-(4-fluorophenyl)ethyl]piperidine-4-carboxamide;2,2,2-trifluoroacetic acidYield 128%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-fluoro-phenyl)-4-[(S)-1-(4-fluoro-phenyl)-ethylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester (735 mg, 1.653 mmol) in dichloromethane (8 mL) at 0° C. was added slowly trifluoroacetic acid (1.78 mL, 23.148 mmol) and stirring continued for 12 h at room temperature. The solvent was removed under reduced pressure. Toluene was added to the residue and evaporated under reduced pressure which was repeated two times. The residue was dried under high vacuum to yield 970 mg 4-(4-fluoro-phenyl)-piperidine-4-carboxylic acid [(S)-1-(4-fluoro-phenyl)-ethyl]-amide; compound with trifluoro-acetic acid. MS ISP (m/e): 345.3 [(M+H)+].

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionToluene was added to the residue
  3. customevaporated under reduced pressure which
  4. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-144ca213ab544457ace41645d71840df
Source dataset
uspto-grants-2012_12
Patent number
US08324250B2

Reaction notes

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