Water → HCID 13236393, compound

HRID 1649255Notes

Reaction equation

HRID 1649255 reaction equation
Br.[N:2]1([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]3)=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1.O>CN(C=O)C>[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([N:5]2[CH2:6][CH2:7][N:2]([C:8]3[CH:17]=[C:16]4[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]4)=[CH:10][CH:9]=3)[CH2:3][CH2:4]2)=[O:32])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 20480595HCID 20480595, compound

Product 1

HCID 13236393HCID 13236393, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 800 mg of 7-(1-piperazinyl)-3,4-dihydrocarbostyril hydrobromide in 10 ml of DMF was added 1.2 ml of triethylamine, and then a solution of 730 mg of 4-chlorobenzoyl chloride in 2 ml of DMF was added dropwise to the mixture while stirring. After completion of addition, the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into a large amount of water. Crystals which formed were collected by filtration, washed with water and dried. The crystals were purified through silica gel column chromatography and recrystallized from chloroform-methanol to give 700 mg of 7-[4-(4-chlorobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 289°-291° C., colorless powders.

Workup

  1. additionAfter completion of addition
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. customCrystals which formed
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried
  7. customThe crystals were purified through silica gel column chromatography
  8. customrecrystallized from chloroform-methanol

Sources & evidence

ORD record
ord-7bcf3ed46ba04fa596124b380bc7ecc3
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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