Hydrochloric Acid → HCID 20034526, compound

HRID 231101Notes

Reaction equation

HRID 231101 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([C:7]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[NH:25][C:24](=[O:29])[CH2:23][CH2:22]4)=[O:18])[CH2:13][CH2:12]2)=[O:8])=[CH:5][CH:4]=1.[BH4-].[Na+].[ClH:34].C(O)C>CO.CN(C)C=O>[ClH:34].[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH:7]([OH:8])[CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[NH:25][C:24](=[O:29])[CH2:23][CH2:22]4)=[O:18])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 4311764Sodium borohydride2×HCID 13369822HCID 13369822, compound

Product 1

HCID 20034526HCID 20034526, compound

Reagents, catalysts & solvents 1

HCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

2.8 Grams of 6-{4-[2-(4-methoxybenzoyl)ethyl]-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril was suspended in 150 ml of methanol-dimethylformamide [1:1(v/v)] then 0.26 g of sodium borohydride was added thereto at room temperature and stirred for 1 hour. The excess sodium borohydride was decomposed by adding 2M-hydrochloric acid to the reaction mixture, and the solvent was removed by evaporation. The residue was treated with a mixture of water-ethyl acetate, and the organic layer was washed with water, dried then the solvent was removed by evaporation. The residue thus obtained was converted into hydrochloride by adding ethanol-concentrated hydrochloric acid, and the thus obtained hydrochloride was recrystallized from ethanol-water to obtain 0.9 g of 6-{4-[3-(4-methoxyphenyl)-3-hydroxypropyl]-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril monohydrochloride. Melting point: 219°-224° C. (dec.). Colorless powdery substance.

Workup

  1. additionwas added
  2. customthe solvent was removed by evaporation
  3. additionThe residue was treated with a mixture of water-ethyl acetate
  4. washthe organic layer was washed with water
  5. customdried
  6. customthe solvent was removed by evaporation
  7. customThe residue thus obtained
  8. customthe thus obtained hydrochloride was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-eb5a7181f8b04a9aaa81571fb8dbe232
Source dataset
uspto-grants-1989_07
Patent number
US04845100

Reaction notes

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