3,5-Dichlorobenzoyl chloride → 5-[4-(3,5-Dichlorobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

HRID 1649212Notes

Reaction equation

HRID 1649212 reaction equation
Br.[N:2]1([C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH2:10][CH2:11][C:12](=[O:18])[NH:13]3)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])O.[Na+].N1(C2C=CC=C3C=2CCC(=O)N3)CCNCC1.[Cl:41][C:42]1[CH:43]=[C:44]([CH:48]=[C:49]([Cl:51])[CH:50]=1)[C:45](Cl)=[O:46]>CN(C=O)C.C(N(CC)CC)C>[Cl:41][C:42]1[CH:43]=[C:44]([CH:48]=[C:49]([Cl:51])[CH:50]=1)[C:45]([N:5]1[CH2:6][CH2:7][N:2]([C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH2:10][CH2:11][C:12](=[O:18])[NH:13]3)[CH2:3][CH2:4]1)=[O:46]

Participants

7

Reactant 4

HCID 761913,5-Dichlorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 11630008HCID 11630008, compoundHCID 204805915-(1-Piperazinyl)-3,4-dihydrocarbostyril monohydrobromide

Product 1

HCID 132363365-[4-(3,5-Dichlorobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyrilYield 39.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

5-(1-Piperazinyl)-3,4-dihydrocarbostyril monohydrobromide (3.5 g) was suspended in 40 ml DMF. After adding 960 mg of sodium hydrogencarbonate, the suspension was stirred at room temperature for 30 minutes to convert the starting compound to 5-(1-piperazinyl)-3,4-dihydrocarbostyril. Then, to the mixture was added 2.34 ml of triethylamine and the mixture was stirred at room temperature while slowly adding dropwise 10 ml of DMF solution containing 3.0 g of 3,5-dichlorobenzoyl chloride. After completion of addition the reaction mixture was stirred for 40 minutes. The reaction mixture was poured into a large amount of saturated saline solution and extracted with chloroform. The extract was washed with saturated sodium hydrogencarbonate solution and subsequently with water and dried over anhydrous sodium sulfate. Chloroform was distilled off and residual crystals were recrystallized from methanol-chloroform to give 1.8 g of 5-[4-(3,5-dichlorobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 255°-257° C., colorless needles.

Workup

  1. stirringthe mixture was stirred at room temperature
  2. additionAfter completion of addition the reaction mixture
  3. stirringwas stirred for 40 minutes
  4. additionThe reaction mixture was poured into a large amount of saturated saline solution
  5. extractionextracted with chloroform
  6. washThe extract was washed with saturated sodium hydrogencarbonate solution and subsequently with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationChloroform was distilled off
  9. customresidual crystals were recrystallized from methanol-chloroform

Sources & evidence

ORD record
ord-5d8621d17fec44beafca764480b271d7
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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