Sodium Bicarbonate → 6-[4-(4-Acetyloxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

HRID 1649247Notes

Reaction equation

HRID 1649247 reaction equation
Br.[N:2]1([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]3)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])O.[Na+].N1(C2C=C3C(=CC=2)NC(=O)CC3)CCNCC1.[C:41]([O:44][C:45]1[CH:53]=[CH:52][C:48]([C:49](Cl)=[O:50])=[CH:47][CH:46]=1)(=[O:43])[CH3:42]>CN(C=O)C.O.C(N(CC)CC)C>[C:41]([O:44][C:45]1[CH:53]=[CH:52][C:48]([C:49]([N:5]2[CH2:6][CH2:7][N:2]([C:8]3[CH:9]=[C:10]4[C:15](=[CH:16][CH:17]=3)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]4)[CH2:3][CH2:4]2)=[O:50])=[CH:47][CH:46]=1)(=[O:43])[CH3:42]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 2756254p-Acetoxybenzoyl chlorideHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 132363086-(1-Piperazinyl)-3,4-dihydrocarbostyril hydrobromide

Product 1

HCID 204805976-[4-(4-Acetyloxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

A suspension of 1.0 g of 6-(1-piperazinyl)-3,4-dihydrocarbostyril monohydrobromide in 10 ml of DMF was added 296 mg of sodium hydrogencarbonate and stirred at room temperature for 30 minutes to convert the compound to 6-piperazinyl-3,4-dihydrocarbostyril, to which was added 0.62 ml of triethylamine. Then, a solution of 605 mg of 4-acetyloxybenzoyl chloride in 5 ml of DMF was slowly added dropwise to the mixture. After completion of addition, the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into a large amount of water and extracted with chloroform. The extract was washed serially with saturated aqueous sodium hydrogencarbonate solution and with water and then dried over anhydrous sodium sulfate. Chloroform was distilled off to give 6-[4-(4-acetyloxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril.

Workup

  1. additionAfter completion of addition
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionextracted with chloroform
  4. washThe extract was washed serially with saturated aqueous sodium hydrogencarbonate solution and with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationChloroform was distilled off

Sources & evidence

ORD record
ord-5ce33e036acc4c32a542b76e163be5b9
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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