Water → HCID 14099817, compound

HRID 1460682Notes

Reaction equation

HRID 1460682 reaction equation
Cl.Cl[CH:3]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]([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)=[O:13])[CH2:8][CH2:7]1.Cl.[CH3:32][NH2:33].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:32][NH:33][CH:3]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]([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)=[O:13])[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6364545Methylamine hydrochlorideHCID 14099816HCID 14099816, compound

Product 1

HCID 14099817HCID 14099817, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

One gram of 6-[4-(3-chloro-3-phenylpropyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril.hydrochloride, 0.17 g of methylamine.hydrochloride and 1.2 g of potassium carbonate were dispersed in 20 ml of acetonitrile and the dispersion was stirred at 60° C. for 4 hours. After the reaction was completed, the reaction mixture was poured into water then extracted with methylene chloride. The extract was dried with anhydrous sodium carbonate, then the solvent was removed by evaporation. Thus obtained residue was purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol =20:1), then the desired product was converted into a citrate, and recrystallized from ethanol-water to yield 0.5 g of 6-[4-(3-methylamino-3-phenylpropyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril. dicitrate. White powdery substance. Melting point: 150° C.-156° C. (decomp.).

Workup

  1. extractionthen extracted with methylene chloride
  2. dry with materialThe extract was dried with anhydrous sodium carbonate
  3. customthe solvent was removed by evaporation
  4. customThus obtained residue was purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol =20:1)
  5. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-142e1982cbdd4ac09cfc0aa5a90fac6a
Source dataset
uspto-grants-1991_12
Patent number
US05071856

Reaction notes

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