Water → 3,3-Bis(4-chlorophenyl)pyrrolidin-2-one

HRID 2408851Notes

Reaction equation

HRID 2408851 reaction equation
O.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)([CH2:15][C:16]#[N:17])[C:10](OCC)=[O:11])=[CH:5][CH:4]=1.N.CO>[Ni].CO>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[CH2:15][CH2:16][NH:17][C:10]2=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 21705897Ammonia methanolHCID 67387582Ethyl 2,2-bis(4-chlorophenyl)-3-cyanopropanoate

Product 1

HCID 673870023,3-Bis(4-chlorophenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A 500 mL stainless steel pressure bottle was charged with a Raney®-nickel 2800/water slurry (23.60 g, 402 mmol), followed by addition of the product from Example 25A (5.90 g, 16.9 mmol) and a solution of 7M NH3—CH3OH (30 mL)/CH3OH (120 mL). The reaction mixture was stirred at ambient temperature under an atmosphere of 30 psi H2 for 4 hours. The mixture was filtered through a nylon membrane and concentrated in vacuo. The crude product was slurried in 5% ethyl acetate/hexane, and the solid was collected by filtration to yield the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.13 (s, 1H), 7.41-7.35 (m, 4H), 7.35-7.30 (m, 4H), 3.18 (t, J=6.4, 2H), 2.72 (t, J=6.4, 2H); MS (DCI+) m/z 323 (M+NH4)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated in vacuo
  3. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-4d94df2a8bba4670ba1bfa6245edc8b2
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

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