Acetic Anhydride → HCID 19027726, compound

HRID 742979Notes

Reaction equation

HRID 742979 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:27]4[C:22](=[C:23]([Cl:28])[CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][C:18]3=[O:19])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[ClH:28].[C:29]([NH:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:27]4[C:22](=[C:23]([Cl:28])[CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][C:18]3=[O:19])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 11795203HCID 11795203, compound

Product 1

HCID 19027726HCID 19027726, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

1-{3-[4-(3-aminophenyl)-1-piperazinyl]propyl}-5-chloro-3,4-dihydrocarbostyril (1 g) was dissolved in 10 ml of chloroform, 5 ml of acetic anhydride and 0.1 g of 4-dimethylaminopyridine were added, and the mixture was heated under reflux for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography and then converted to the hydrochloride form, which was recrystallized from ethanol to give 900 mg of 1-{3-[4-(3-acetylaminophenyl)-1-piperazinyl]propyl}-5-chloro-3,4-dihydrocarbostyril hydrochloride as colorless needles.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography
  5. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-4be372c377c14b0e9ebd27cca4017395
Source dataset
uspto-grants-1996_09
Patent number
US05556857

Reaction notes

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