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

HRID 1285462Notes

Reaction equation

HRID 1285462 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-dihyro-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. for 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-74be98197ac049539a21c8b767388945
Source dataset
uspto-grants-1986_01
Patent number
US04567187

Reaction notes

Loading…