Hydrochloric Acid → 5-[2-Hydroxy-3-(4-phenylpiperazinyl)propoxy]-3,4-dihydro carbostyril monohydrochloride

HRID 569955Notes

Reaction equation

HRID 569955 reaction equation
[O:1]1[CH2:16][CH:2]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.[C:17]1([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[ClH:29].C(O)C>CO.CC(C)=O>[ClH:29].[OH:1][CH:2]([CH2:16][N:26]1[CH2:27][CH2:28][N:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:24][CH2:25]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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 70961-PhenylpiperazineHCID 128994235-[(Oxiran-2-yl)methoxy]-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 128994275-[2-Hydroxy-3-(4-phenylpiperazinyl)propoxy]-3,4-dihydro carbostyril monohydrochloride

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

4.4 Grams of 5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril and 3.4 g of 4-phenylpiperazine are dispersed in 60 ml of methanol and reacted at 50°-60° C. for 3 hours. After the reaction is completed, the reaction mixture is concentrated under a reduced pressure. To the residue thus obtained are added 5 ml of concentrated hydrochloric acid and 30 ml of ethanol to dissolve the residue uniformly and further 200 ml of acetone are added. The crystals precipitated are collected by filtration and dried. Recrystallization from water obtains 6.5 g of 5-[2-hydroxy-3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril monohydrochloride in the form of colorless needle-like crystals with a melting point of 239°-241° C.

Workup

  1. customreacted at 50°-60° C. for 3 hours
  2. concentrationthe reaction mixture is concentrated under a reduced pressure
  3. customTo the residue thus obtained
  4. dissolutionto dissolve the residue uniformly
  5. customThe crystals precipitated
  6. filtrationare collected by filtration
  7. customdried
  8. customRecrystallization from water

Sources & evidence

ORD record
ord-f448c440e4f4405484860cae6cb7d71e
Source dataset
uspto-grants-1988_03
Patent number
US04734416

Reaction notes

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