Acetone → HCID 12899550, compound

HRID 569966Notes

Reaction equation

HRID 569966 reaction equation
[OH:1][CH:2]([CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:15])[NH:10]2.[CH3:29][C:30](C)=[O:31].C(Cl)(=O)C.N.O>O>[C:30]([O:1][CH:2]([CH2:16][N:17]1[CH2:18][CH2:19][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][CH2:22]1)[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:15])[NH:10]2)(=[O:31])[CH3:29]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6367Acetyl chlorideHCID 12896473Azane;hydrateHCID 12899426HCID 12899426, compound

Product 1

HCID 12899550HCID 12899550, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 Grams of 5-[2-hydroxy-3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril are mixed with 30 ml of acetone and further 12 ml of acetyl chloride are added followed by heating for 10 hours under refluxing conditions. After cooling the reaction mixture, the product precipitated is collectd by filtration and washed with acetone. The crude crystals thus obtained are dissolved in 80 ml of water and made basic with ammonia-water, then extracted with chloroform, dried and chloroform is removed by distillation. The residue is purified by silica gel chromatography to obtain 0.5 g of 5-[2-acetyloxy-3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril in the form of colorless crystals with a melting point of 159°-161° C.

Workup

  1. additionare added
  2. temperatureby heating for 10 hours under refluxing conditions
  3. temperatureAfter cooling the reaction mixture
  4. customthe product precipitated
  5. filtrationis collectd by filtration
  6. washwashed with acetone
  7. customThe crude crystals thus obtained
  8. extractionextracted with chloroform
  9. customdried
  10. customchloroform is removed by distillation
  11. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-f3723f18caa84ea1818b9ca52252c323
Source dataset
uspto-grants-1988_03
Patent number
US04734416

Reaction notes

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