Acetone → HCID 12899550, compound

HRID 621565Notes

Reaction equation

HRID 621565 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 collected 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 collected 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-050cf1a242de4e9b876384a9f4dee34d
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Reaction notes

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