Hydrochloric Acid → HCID 13369832, compound

HRID 1262861Notes

Reaction equation

HRID 1262861 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 adjust 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 1 N-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 1 N-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-e7c6bab8a02d4bdbb312f7856bf6c14a
Source dataset
uspto-grants-1984_06
Patent number
US04454130

Reaction notes

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