Lithium Hydroxide → Aniracetam

HRID 1164310Notes

Reaction equation

HRID 1164310 reaction equation
[H-].[Li+].C[O:4][C:5]1[NH:6][CH2:7][CH2:8][CH:9]=1.[CH3:10][O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1.[OH-].[Li+]>O.C(OCC)(=O)C.C1C=CC=CC=1>[CH3:10][O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([N:6]2[CH2:7][CH2:8][CH2:9][C:5]2=[O:4])=[O:17])=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 3939Lithium HydroxideHCID 7477p-Anisoyl chlorideHCID 62714Lithium hydrideHCID 127618282-Methoxypyrroline

Product 1

HCID 2196Aniracetam

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

276 mg. of lithium hydride (98%), 40 ml. of benzene and 4.2 g. of 2-methoxypyrroline are boiled at reflux for 2 hours under nitrogen and while stirring well. After cooling to 25° C., 6.6 g. of p-methoxybenzoyl chloride dissolved in 25 ml. of benzene are added and the resulting mixture is stirred under reflux for 2 hours and at room temperature for 16 hours. 100 ml. of ethyl acetate followed by 3.0 g. of lithium hydroxide (98%) dissolved in 25 ml. of water are added to the mixture at room temperature within 15 minutes. The organic phase is washed neutral with water, dried over sodium sulfate and evaporated under reduced pressure. After recrystallization from ethanol, there is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone having a melting point of 119°-120° C.

Workup

  1. temperatureat reflux for 2 hours under nitrogen
  2. stirringthe resulting mixture is stirred
  3. temperatureunder reflux for 2 hours and at room temperature for 16 hours
  4. washThe organic phase is washed neutral with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-21370e1556bb4704875bf8fa4b26e30f
Source dataset
uspto-grants-1983_01
Patent number
US04369139

Reaction notes

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