Aniline → 6-[1-Hydroxy-4-(4-phenyl-1-piperazinyl)butyl]-3,4-dihydrocarbostyril

HRID 1263127Notes

Reaction equation

HRID 1263127 reaction equation
[OH:1][CH:2]([C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[CH2:17][CH2:16]2)[CH2:3][CH2:4][CH2:5][N:6]([CH2:10][CH2:11]Cl)[CH2:7][CH2:8]Cl.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:1][CH:2]([C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[CH2:17][CH2:16]2)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:11][N:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 202294566-{1-Hydroxy-4-[bis-chloroethyl-amino]butyl}-3,4-dihydrocarbostyril

Product 1

HCID 128335176-[1-Hydroxy-4-(4-phenyl-1-piperazinyl)butyl]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.5 Grams of 6-{1-hydroxy-4-[bis-chloroethyl-amino]butyl}-3,4-dihydrocarbostyril, 1.5 g of aniline and 2.2 g of potassium carbonate were mixed in 150 ml of ethanol and the mixture was refluxed by heating for 24 hours. The reaction mixture was concentrated under a reduced pressure and the residue thus obtained was extracted with chloroform. The chloroform layer was washed with water, dried and chloroform was removed by distillation. The residue thus obtained was separated and purified by a preparative thin layer chromatography and recrystallized from isopropanol to obtain 0.2 g of 6-[1-hydroxy-4-(4-phenyl-1-piperazinyl)butyl]-3,4-dihydrocarbostyril in colorless needle-like crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 24 hours
  3. concentrationThe reaction mixture was concentrated under a reduced pressure
  4. customthe residue thus obtained
  5. extractionwas extracted with chloroform
  6. washThe chloroform layer was washed with water
  7. customdried
  8. customchloroform was removed by distillation
  9. customThe residue thus obtained
  10. customwas separated
  11. custompurified by a preparative thin layer chromatography
  12. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-0afc717f790c4a658541b70e5143eace
Source dataset
uspto-grants-1984_06
Patent number
US04455422

Reaction notes

Loading…