Sodium hydride → 4-Benzhydryl-1-[2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)ethyl]piperazin-2-one

HRID 1667136Notes

Reaction equation

HRID 1667136 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][C:28]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27]1=[O:43]>CN(C)C=O>[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][C:28]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:27]2=[O:43])[C:16](=[O:20])[CH2:15]1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 119759334-Benzhydrylpiperazin-2-oneHCID 673587991-(2-Bromoethyl)-3,3-diphenylpyrrolidin-2-one

Product 1

HCID 674471834-Benzhydryl-1-[2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)ethyl]piperazin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of product from Example 64C (0.11 g, 0.4 mmol)) in N,N-dimethylformamide was added a 60% dispersion of sodium hydride in mineral oil (0.03 g, 0.75 mmol) and the reaction mixture was stirred at room temperature for 1 hour. Then 1-(2-bromoethyl)-3,3-diphenylpyrrolidin-2-one (Example 64B, 0.142 g, 0.4 mmol) was added, and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated and partitioned in water/methylene chloride. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed, eluting first with 5% ethyl acetate/hexane and then eluting the title compound with 15% methanol/methylene chloride. 1H NMR (300 MHz, CDCl3) δ ppm 7.31 (m, 20H), 3.48 (t, J=6.44 Hz, 2H), 3.42 (m, 2H), 3.28 (m, 2H), 3.12 (s, 2H), 2.70 (m, 2H), 2.66 (m, 2H), 2.42 (m, 2H); MS (ESI+) m/z 530 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned in water/methylene chloride
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed
  8. washeluting first with 5% ethyl acetate/hexane
  9. washeluting the title compound with 15% methanol/methylene chloride

Sources & evidence

ORD record
ord-48d1b5b6f67b4f1791adc8911dbfd24d
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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