Sodium Chloride → HCID 13064796, compound

HRID 1979779Notes

Reaction equation

HRID 1979779 reaction equation
[C:1]([C:4]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH2:18][CH2:17]3)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:33]I.[Cl-].[Na+]>CN(C)C=O>[CH3:33][N:20]1[C:21]2[C:16](=[CH:15][C:14]([O:13][CH2:12][CH2:11][CH2:10][N:7]3[CH2:6][CH2:5][C:4]([C:1](=[O:3])[CH3:2])([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:9][CH2:8]3)=[CH:23][CH:22]=2)[CH2:17][CH2:18][C:19]1=[O:24]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20438585HCID 20438585, compound

Product 1

HCID 13064796HCID 13064796, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 Grams of 6-[3-(4-acetyl-4-phenyl-1-piperidyl)propoxy]-3,4-dihydrocarbostyril and 0.25 g of sodium hydride (50% in oil) were mixed in 30 ml of dimethylformamide and stirred for 1 hour, then 0.7 g of methyl iodide was added thereto and stirred at a room temperature for 12 hours. The reaction mixture was poured into 80 ml of saturated sodium chloride solution and the organic layer was extracted with chloroform and the chloroform layer was washed with water and dried. Then the chloroform was removed by distillation and the residue was crystallized with hexane. The crude crystals were recrystallized from ligroin to obtain 1.7 g of 1-methyl-6-[3-(4-acetyl-4-phenyl-1-piperidyl)propoxy]-3,4-dihydrocarbostyril as in the form of colorless needle-like crystals. Melting point: 115°-117° C.

Workup

  1. stirringstirred at a room temperature for 12 hours
  2. extractionthe organic layer was extracted with chloroform
  3. washthe chloroform layer was washed with water
  4. customdried
  5. customThen the chloroform was removed by distillation
  6. customthe residue was crystallized with hexane
  7. customThe crude crystals were recrystallized from ligroin

Sources & evidence

ORD record
ord-3ec86f6a652f491f9478e2459abd76fa
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

Loading…