Pyridine → 6-[1-Oxo-4-(4-phenyl-4-acetyl-1-piperidyl)butyl]-3,4-dihydrocarbostyril

HRID 2291204Notes

Reaction equation

HRID 2291204 reaction equation
[O:1]=[C:2]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2)[CH2:3][CH2:4][CH2:5]Cl.N1C=CC=CC=1.[C:24]1([C:30]2([C:36](=[O:38])[CH3:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[O:1]=[C:2]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2)[CH2:3][CH2:4][CH2:5][N:33]1[CH2:32][CH2:31][C:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:36](=[O:38])[CH3:37])[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 1015214-Acetyl-4-phenylpiperidineHCID 516892Sodium BicarbonateHCID 128335166-(4-Chlorobutyryl)-3,4-dihydrocarbostyril

Product 1

HCID 131208206-[1-Oxo-4-(4-phenyl-4-acetyl-1-piperidyl)butyl]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.6 Grams of 6-(1-oxo-4-chlorobutyl)-3,4-dihydro-carbostyril, 1.2 g of pyridine and 2.7 g of 4-phenyl-4-acetyl-piperidine were mixed in 30 ml of dimethylformamide and stirred at 70°-80° C. foir 7 hours. The reaction mixture was poured into 100 ml of 5%-sodium hydrogencarbonate aqueous solution and the organic layer was extracted with chloroform then the chloroform layer was washed with water, dried and chloroform was removed by distillation. The residue thus obtained was recrystallized from ethanol to obtain 6-[1-oxo-4-(4-phenyl-4-acetyl-1-piperidyl)butyl]-3,4-dihydrocarbostyril in light yellow plate-like crystals. Yield: 2.1 g. Melting point: 166°-167° C.

Workup

  1. extractionthe organic layer was extracted with chloroform
  2. washthe chloroform layer was washed with water
  3. customdried
  4. customchloroform was removed by distillation
  5. customThe residue thus obtained
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-901bb46f2a204b10b0bb31e51fd7f844
Source dataset
uspto-grants-1986_10
Patent number
US04619932

Reaction notes

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