Hydrochloric Acid → 3,4-Dihydro-5-[2-hydroxy-3-(4-(ethoxycarbonylamino)-1-piperidyl)propoxy]carbostyril hydrochloride

HRID 1090704Notes

Reaction equation

HRID 1090704 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:12])[O:9][CH2:10][CH3:11])[CH2:3][CH2:2]1.[O:13]1[CH2:28][CH:14]1[CH2:15][O:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH2:19][CH2:20][C:21](=[O:27])[NH:22]2.[ClH:29]>C(O)C>[ClH:29].[OH:13][CH:14]([CH2:28][N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8]([O:9][CH2:10][CH3:11])=[O:12])[CH2:5][CH2:6]1)[CH2:15][O:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH2:19][CH2:20][C:21](=[O:27])[NH:22]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 128994235-[(Oxiran-2-yl)methoxy]-3,4-dihydroquinolin-2(1H)-oneHCID 15595030ethyl N-(piperidin-4-yl)carbamate

Product 1

HCID 199137413,4-Dihydro-5-[2-hydroxy-3-(4-(ethoxycarbonylamino)-1-piperidyl)propoxy]carbostyril hydrochlorideYield 56.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-piperidylcarbamate (2 g), from Preparation 4, and 5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril (2.54 g), from Preparation 5, were dissolved in ethanol (50 mL) and the resulting solution was heated under reflux for 6 hours and then cooled to room temperature. Concentrated hydrochloric acid (1 mL) was added. A white product precipitated, which was collected by filtration. The crude product was recrystallized from ethanol to yield 2.8 g (56.5%) of 3,4-dihydro-5-[2-hydroxy-3-(4-(ethoxycarbonylamino)-1-piperidyl)propoxy]carbostyril hydrochloride, m.p. 232°-234° C. (dec.).

Workup

  1. customfrom Preparation 5
  2. temperaturethe resulting solution was heated
  3. temperatureunder reflux for 6 hours
  4. customA white product precipitated
  5. filtrationwhich was collected by filtration
  6. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-589071c247414f89aac80c3d701901c6
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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