Ammonium formate → HCID 22240781, compound

HRID 892266Notes

Reaction equation

HRID 892266 reaction equation
C([O-])=O.[NH4+].C(OC([N:15]1[CH2:20][CH2:19][C:18]([CH2:27][C:28](=[O:39])[NH:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=O)C1C=CC=CC=1>CO.[Pd]>[F:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:31][CH2:30][NH:29][C:28](=[O:39])[CH2:27][C:18]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 23600719HCID 23600719, compound

Product 1

HCID 22240781HCID 22240781, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (1.00 g) was added to a solution of 4-{[2-(2-fluoro-phenyl)-ethylcarbamoyl]-methyl}-4-phenyl-piperidine-1-carboxylic acid benzyl ester (0.520 g, 1.10 mmol) in methanol (50 mL) containing 10% palladium/carbon (0.500 g) and stirred for 4 h. The reaction mixture was filtered through celite and concentrated under reduced pressure. The crude product was taken up in 1M sodium hydroxide (100 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were collected and concentrated under reduced pressure to give 0.328 g (87%) of N-[2-(2-fluoro-phenyl)-ethyl]-2-(4-phenyl-piperidin-4-yl)-acetamide. LRMS m/z 341.1 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. customThe organic layers were collected
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-add1f7cb990d4bc89099ea344112d427
Source dataset
uspto-grants-2006_02
Patent number
US07005436B2

Reaction notes

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