Sodium hydride → 2-(1-Benzhydryl-2-oxo-pyrrolodin-3-yl-amino)-N,N-diphenyl acetamide

HRID 1786561Notes

Reaction equation

HRID 1786561 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]1=[O:20].Br[CH2:22][C:23]([N:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24].[H-].[Na+]>CN(C=O)C>[CH:7]([N:4]1[CH2:5][CH2:6][CH:2]([NH:1][CH2:22][C:23]([N:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:24])[C:3]1=[O:20])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2320412-Bromo-n,n-diphenylacetamideHCID 575975623-Amino-1-benzhydryl-pyrrolidin-2-one

Product 1

HCID 575975682-(1-Benzhydryl-2-oxo-pyrrolodin-3-yl-amino)-N,N-diphenyl acetamideYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-amino-1-benzhydryl-pyrrolidin-2-one (42) (0.2 g, 0.75 mmol in dry DMF (15 ml) was added 2-bromo-N,N-diphenyl acetamide (0.24 g, 0.82 mmol) and NaH (50 mg) under nitrogen. The reaction mixture was heated at 100 degrees overnight. After cooling, the solvent was evaporated and residue was taken up with ethyl acetate (50 ml) and washed with water (2×10 ml). The organic was dried over MgSO4 and evaporated to dryness. The resulting residue was purified by column chromatography using hexane:ethyl acetate (2:1) to give desired product in 73% yield.

Workup

  1. temperatureThe reaction mixture was heated at 100 degrees overnight
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. washwashed with water (2×10 ml)
  5. dry with materialThe organic was dried over MgSO4
  6. customevaporated to dryness
  7. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-f49a2e9c3a4b49999eae65a12fbe610b
Source dataset
uspto-grants-2009_03
Patent number
US07507760B2

Reaction notes

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