N-[2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamide → N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide

HRID 1178025Notes

Reaction equation

HRID 1178025 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:32])[CH2:15][NH:16][C:17](=[O:31])[C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[O:32]=[C:14]([N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH2:15][NH:16][C:17](=[O:31])[C:18]1[CH:19]=[CH:20][C:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 27671405N-[2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 59559582N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamideYield 100.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under an inert atmosphere, 10% Pd/C (111 mg) was added to a stirred solution of N-[2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamide (490 mg, 1.14 mmol) in MeOH (90 mL). Hydrogen gas was then passed into the reaction mixture by means of a hydrogen filled bladder and the mixture was stirred at room temperature overnight. The mixture was filtered over celite and the celite was washed with MeOH. The filtrate was collected and concentrated under reduced pressure to afford 390 mg (quantitative yield) of N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenoxy-benzamide as a solid. LC-MS purity: 88.65, 1H NMR (CDCl3): δ 7.8 (d, 2H), 7.38 (m, 2H), 7.26 (bs, 1H), 7.18 (tt, 1H), 7.08-7.0 (m, 4H), 4.24 (d, 2H), 3.66 (t, 2H), 3.5 (s, 1H), 3.44 (t, 2H), 2.9 (q, 4H), 2.5-2.6 (m, 1H).

Workup

  1. filtrationThe mixture was filtered over celite
  2. washthe celite was washed with MeOH
  3. customThe filtrate was collected
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ad2e13fe3054ed9926943099dfda10d
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…