Trifluoroacetic acid → 4-(2-Fluoro-benzyl)-piperidine-4-carboxylic acid [2-(4-ethyl-phenyl)-ethyl]-amide

HRID 730200Notes

Reaction equation

HRID 730200 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][C:18]([C:29](=[O:41])[NH:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([CH2:39][CH3:40])=[CH:35][CH:34]=2)([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[F:28])[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[CH2:39]([C:36]1[CH:37]=[CH:38][C:33]([CH2:32][CH2:31][NH:30][C:29]([C:18]2([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]2)=[O:41])=[CH:34][CH:35]=1)[CH3:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 236010764-[2-(4-Ethyl-phenyl)-ethylcarbamoyl]-4-(2-fluoro-benzyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 236009334-(2-Fluoro-benzyl)-piperidine-4-carboxylic acid [2-(4-ethyl-phenyl)-ethyl]-amideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20 mL) was added to a solution 4-[2-(4-ethyl-phenyl)-ethylcarbamoyl]-4-(2-fluoro-benzyl)-piperidine-1-carboxylic acid tert-butyl ester (0.300 g, 0.64 mmol) in dichloromethane (50 mL). After 1 h the reaction mixture was concentrated under reduced pressure, the crude product taken up in 1M sodium hydroxide (50 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were collected, concentrated under reduced pressure and crude product purified by column chromatography to give 0.188 g (80 %) of 4-(2-fluoro-benzyl)-piperidine-4-carboxylic acid [2-(4-ethyl-phenyl)-ethyl]-amide LRMS m/z 369.1 (M+H)+.

Workup

  1. concentrationAfter 1 h the reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. customThe organic layers were collected
  4. concentrationconcentrated under reduced pressure and crude product
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-bb080dc6a3214d65a355ab308a913fdb
Source dataset
uspto-grants-2009_09
Patent number
US07582654B2

Reaction notes

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