Acetic Anhydride → 4-{4-Methoxy-3-[3-(4-phenylpiperazin-1-yl)-2-acetoxypropoxy]phenyl}-2-pyrrolidone

HRID 1856459Notes

Reaction equation

HRID 1856459 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10]2)=[CH:5][C:4]=1[O:15][CH2:16][CH:17]([OH:31])[CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:20]1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10]2)=[CH:5][C:4]=1[O:15][CH2:16][CH:17]([O:31][C:32](=[O:34])[CH3:33])[CH2:18][N:19]1[CH2:20][CH2:21][N:22]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 23345032HCID 23345032, compound

Product 1

HCID 233450234-{4-Methoxy-3-[3-(4-phenylpiperazin-1-yl)-2-acetoxypropoxy]phenyl}-2-pyrrolidoneYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7.5 mmol of 4-{4-methoxy- 3-[3-(4-phenylpiperazin-1-yl)-2-hydroxypropoxy]phenyl}-2-pyrrolidone is dissolved in 50 ml. of dry pyridine. After adding 15 mmol of acetic anhydride, the mixture is heated for 3 hours under reflux. After cooling, the reaction mixture is concentrated under vacuum. The residue is chromatographed over silica gel (acetone/dichloromethane 1:1) and recrystallized from isopropanol, thus obtaining in an 86% yield 4-{4-methoxy-3-[3-(4-phenylpiperazin-1-yl)-2-acetoxypropoxy]phenyl}-2-pyrrolidone, m.p. 128°-133°.

Workup

  1. temperaturethe mixture is heated for 3 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture is concentrated under vacuum
  5. customThe residue is chromatographed over silica gel (acetone/dichloromethane 1:1)
  6. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-92d87f67f852471a9d272654120780ea
Source dataset
uspto-grants-1980_08
Patent number
US04219551

Reaction notes

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