Triphenyl phosphite → Cebaracetam

HRID 2166340Notes

Reaction equation

HRID 2166340 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][N:11]([CH2:13][C:14]([OH:16])=O)[C:10](=[O:17])[CH2:9]2)=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][C:19]1=[O:24].P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][N:11]([CH2:13][C:14]([N:21]3[CH2:22][CH2:23][NH:18][C:19](=[O:24])[CH2:20]3)=[O:16])[C:10](=[O:17])[CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7540Triphenyl phosphiteHCID 231360Piperazin-2-oneHCID 230395272-[4-(p-Chlorophenyl)-2-oxopyrrolidin-1-yl]-acetic acid

Product 1

HCID 65919Cebaracetam

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

82.5 g (325 mmol) of 2-[4-(p-chlorophenyl)-2-oxopyrrolidin-1-yl]-acetic acid, 32.5 g (325 mmol) of piperazin-2-one (ketopiperazine) and 100.8 g (325 mmol) of freshly distilled triphenyl phosphite are melted at 180°. The whole is allowed to cool to 130° and left to stand for 5 hours. The solidified reaction mass is cooled to room temperature and stirred for 1 hour with 300 ml of dichloromethane. The whole is filtered with suction, washed three times with 150 ml of dichloromethane each time and allowed to dry in the air. 1-[4-(p-chlorophenyl)-2-oxopyrrolidin-1-ylacetyl]-3-oxopiperazine having a melting point of 208°-210° is obtained and can be purified further by dissolving in 200 ml of hot acetic acid, adding 800 ml of water and crystallising in an ice bath.

Workup

  1. temperatureto cool to 130°
  2. waitleft
  3. filtrationThe whole is filtered with suction
  4. washwashed three times with 150 ml of dichloromethane each time
  5. customto dry in the air

Sources & evidence

ORD record
ord-4f3ce58b042044209c1fcf68c59d7d0e
Source dataset
uspto-grants-1990_07
Patent number
US04945092

Reaction notes

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