Hydrochloric Acid → HCID 13369835, compound

HRID 1153997Notes

Reaction equation

HRID 1153997 reaction equation
[OH:1][CH:2]([CH3:23])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17](=[O:22])[CH2:16][CH2:15]3)=[O:11])[CH2:6][CH2:5]1.[C:24]([Cl:27])(=[O:26])[CH3:25].C(=O)(O)[O-].[Na+].Cl>ClCCl.CO.C(N(CC)CC)C>[ClH:27].[C:24]([O:1][CH:2]([CH3:23])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17](=[O:22])[CH2:16][CH2:15]3)=[O:11])[CH2:6][CH2:5]1)(=[O:26])[CH3:25]

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 13369832HCID 13369832, compound

Product 1

HCID 13369835HCID 13369835, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

0.5 Gram of 6-[4-(2-hydroxypropyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril and 0.3 ml of triethylamine were dissolved in 10 ml of dichloromethane, the mixture was stirred at a room temperature, 0.15 g of acetyl chloride was added slowly thereto and further stirred at a room temperature for 1 hour. The reaction mixture was poured into a saturated sodium bicarbonate aqueous solution and extracted with chloroform. The organic layer was washed with water and a saturated sodium chloride aqueous sodium and extracted with chloroform. The organic layer was washed with water and a saturated sodium chloride aqueous solution then dried with anhydrous sodium sulfate. The solvent was removed by distillation under a reduced pressure and the residue obtained was treated by means of a silica gel column chromatography, then the objective product was dissolved in methanol and converted into the hydrochloride by adding a concentrated hydrochloric acid. Recrystallized from water-acetone to obtain 0.22 g of 6-[4-(2-acetoxypropyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril monohydrochloride. Melting point: 239°-241° C. (decomposed)

Workup

  1. stirringfurther stirred at a room temperature for 1 hour
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water
  4. extractiona saturated sodium chloride aqueous sodium and extracted with chloroform
  5. washThe organic layer was washed with water
  6. dry with materiala saturated sodium chloride aqueous solution then dried with anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under a reduced pressure
  8. customthe residue obtained
  9. additionwas treated by means of a silica gel column chromatography
  10. customRecrystallized from water-acetone

Sources & evidence

ORD record
ord-d8e6d18e907c48f4b1b780bd37f51785
Source dataset
uspto-grants-1984_12
Patent number
US04487772

Reaction notes

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