Hydrochloric Acid → HCID 13369832, compound

HRID 1153998Notes

Reaction equation

HRID 1153998 reaction equation
Cl.[C:2]([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)(=[O:4])[CH3:3].[BH4-].[Na+].Cl>CO>[OH:4][CH:2]([CH3:3])[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20435643HCID 20435643, compound

Product 1

HCID 13369832HCID 13369832, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.76 Grams of 6-(4-acetylmethyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril monohydrochloride was dissolved in 50 ml of methanol, under ice-cooled condition, 0.44 g of sodium borohydride (NaBH4) was added slowly and then stirred at a room temperature for 1 hour. After the reaction was completed, a concentrated hydrochloric acid was added to ajust the pH of the reaction mixture to about pH 1, then most portion of the solvent was removed by distillation under a reduced pressure and the residue was extracted with 1N-NaOH-chloroform. The organic layer was washed with water and dried with anhydrous sodium sulfate, then the solvent was removed by distillation. The residue obtained was treated by means of a column chromatography and recrystallized from ethanol to obtain 2.26 g of 6-[4-(2-hydroxypropyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril. Colorless flake-like crystals. Melting point: 156°-157.5° C.

Workup

  1. additionwas added slowly
  2. custommost portion of the solvent was removed by distillation under a reduced pressure
  3. extractionthe residue was extracted with 1N-NaOH-chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was removed by distillation
  7. customThe residue obtained
  8. additionwas treated by means of a column chromatography
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b17568346f2e4f50a3f9c5743f462436
Source dataset
uspto-grants-1984_12
Patent number
US04487772

Reaction notes

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