Sodium Chloride → 1-Methyl-6-[1-oxo-3-(4-phenyl-1-piperidyl)-propyl]-3,4-dihydrocarbostyril monohydrochloride

HRID 2291205Notes

Reaction equation

HRID 2291205 reaction equation
[O:1]=[C:2]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]2)[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[H-].[Na+].[CH3:30]I.[Cl-:32].[Na+]>CN(C)C=O>[ClH:32].[CH3:30][N:23]1[C:24]2[C:19](=[CH:18][C:17]([C:2](=[O:1])[CH2:3][CH2:4][N:5]3[CH2:10][CH2:9][CH:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:7][CH2:6]3)=[CH:26][CH:25]=2)[CH2:20][CH2:21][C:22]1=[O:27]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 131208226-[1-Oxo-3-(4-phenyl-1-piperidyl)propyl]-3,4-dihydrocarbostyril

Product 1

HCID 131208351-Methyl-6-[1-oxo-3-(4-phenyl-1-piperidyl)-propyl]-3,4-dihydrocarbostyril monohydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.8 Grams of 6-[1-oxo-3-(4-phenyl-1-piperidyl)-propyl]-3,4-dihydrocarbostyril and 0.24 g of sodium hydride (50% in mineral oil) were mixed in 50 ml of dimethylformamide and the mixture was stirred at a room temperature for 3 hours. Then 0.8 g of methyl iodide was added thereto and stirred at a room temperature for 3 hours. The reaction mixture was poured into 150 ml of saturated sodium chloride aqueous solution and the organic layer was extracted with chloroform. The chloroform layer was washed with water, dried and chloroform was removed by distillation. The residue thus obtained was isolated and purified by preparative thin-layer chromatography and the desired product was converted into the hydrochloride then recrystallized from ethanol-water to obtain 1.5 g of 1-methyl-6-[1-oxo-3-(4-phenyl-1-piperidyl)-propyl]-3,4-dihydrocarbostyril monohydrochloride in light yellow plate-like crystals. Melting point: 213°-214° C. (decomposed).

Workup

  1. stirringstirred at a room temperature for 3 hours
  2. extractionthe organic layer was extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. customdried
  5. customchloroform was removed by distillation
  6. customThe residue thus obtained
  7. customwas isolated
  8. custompurified by preparative thin-layer chromatography
  9. customthen recrystallized from ethanol-water

Sources & evidence

ORD record
ord-d0c36ef010d3428fb96daac3d7c2c57f
Source dataset
uspto-grants-1986_10
Patent number
US04619932

Reaction notes

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