p-Anisoyl chloride → Aniracetam

HRID 1164311Notes

Reaction equation

HRID 1164311 reaction equation
C[O:2][C:3]1[NH:4][CH2:5][CH2:6][CH:7]=1.[CH3:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1>C1C=CC=CC=1>[CH3:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([N:4]2[CH2:5][CH2:6][CH2:7][C:3]2=[O:2])=[O:15])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 127618282-Methoxypyrroline

Product 1

HCID 2196Aniracetam

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

4.2 g. of 2-methoxypyrroline are dissolved in 25 ml. of benzene and treated at room temperature with 6.6 g. of p-methoxybenzoyl chloride dissolved in 30 ml. of benzene. The mixture is stirred at room temperature for 60 minutes and at reflux for 4 hours. 30 ml. of benzene are then added and the mixture is boiled at reflux for a further 24 hours. The volatile constituents are distilled off, the residue is taken up in ethanol, the mixture is concentrated, the residue is triturated with diethyl ether, filtered and the filter cake is taken up in ethyl acetate. The ethyl acetate solution is washed with sodium bicarbonate solution and water, dried over sodium sulfate and concentrated. The residue is sublimed in vacuo and there is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 119°-120° C.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureat reflux for a further 24 hours
  3. distillationThe volatile constituents are distilled off
  4. concentrationthe mixture is concentrated
  5. customthe residue is triturated with diethyl ether
  6. filtrationfiltered
  7. washThe ethyl acetate solution is washed with sodium bicarbonate solution and water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ef87cb0e9572455f9b805df694fece6e
Source dataset
uspto-grants-1983_01
Patent number
US04369139

Reaction notes

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