Methanol → N-{1,1-dimethyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-hydroxy-benzamide

HRID 1178003Notes

Reaction equation

HRID 1178003 reaction equation
C([O:8][C:9]1[CH:40]=[CH:39][C:12]([C:13]([NH:15][C:16]([CH3:38])([CH3:37])[C:17](=[O:36])[N:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:35])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])[CH2:20][CH2:19]2)=[O:14])=[CH:11][CH:10]=1)C1C=CC=CC=1.CO>[Pd].C(OCC)(=O)C>[CH3:38][C:16]([NH:15][C:13](=[O:14])[C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:40][CH:39]=1)([CH3:37])[C:17](=[O:36])[N:18]1[CH2:19][CH2:20][N:21]([C:24](=[O:35])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:32])([F:34])[F:33])[CH2:22][CH2:23]1

Participants

5

Reactant 2

HCID 887MethanolHCID 595596074-benzyloxy-N-{1,1-dimethyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide

Product 1

HCID 59559600N-{1,1-dimethyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-hydroxy-benzamideYield 89.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Pd/c (20 mg) was added to a stirred solution of 4-benzyloxy-N-{1,1-dimethyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide (70 mg, 0.12 mmol) in a mixture methanol (2 mL) and ethyl acetate (5 ml) and stirring was continued at room temperature under hydrogen atmosphere for 2 hrs. The mixture was filtered over a bed of celite. The celite was washed with methanol and the filtrate was concentrated under reduced pressure to afford 50 mg (86.2% yield) of N-{1,1-dimethyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-hydroxy-benzamide. LCMS Purity: 95.26%. 1H NMR (DMSO): δ 8.2-8.3 (bs, 1H), 7.5-7.9 (m, 6H), 7.4 (d, 2H), 6.8 (d, 2H), 3.5 (m, 6H), 3 (m, 2H), 1.4 (s, 6H).

Workup

  1. filtrationThe mixture was filtered over a bed of celite
  2. washThe celite was washed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1d57e176aa474daeab4dd0588f0c3599
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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