Ethanol → 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylic acid

HRID 2193173Notes

Reaction equation

HRID 2193173 reaction equation
C(O)C.[CH3:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12](=[O:38])[N:13]2[CH2:16][CH2:17][CH2:18][C:19]2([C:33]([O:35]CC)=[O:34])[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][S:27][C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[CH2:21][CH2:20]2)=[CH:8][CH:7]=1.[OH-].[Na+]>O>[CH3:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12](=[O:38])[N:13]2[CH2:16][CH2:17][CH2:18][C:19]2([C:33]([OH:35])=[O:34])[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][S:27][C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[CH2:21][CH2:20]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 59398305ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate

Product 1

HCID 593983694-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylic acidYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1 mL of an ethanol solution containing 90 mg of ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate, 0.3 mL of 20% aqueous sodium hydroxide solution was added and refluxed with heating for 1.5 hours. Then, more 0.3 mL of 20% aqueous sodium hydroxide solution was added and refluxed with heating for 3 hours. After the reaction mixture was cooled to room temperature, water was added, and the solvent was removed under reduced pressure. Water was added, and adjusted to pH 6.7 with 6.0 mol/L hydrochloric acid. The resulting solid was filtered to afford 57 mg of 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylic acid as a white solid.

Workup

  1. additionwas added
  2. temperaturerefluxed
  3. temperaturewith heating for 1.5 hours
  4. temperaturerefluxed
  5. temperaturewith heating for 3 hours
  6. customthe solvent was removed under reduced pressure
  7. additionWater was added
  8. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-303a4d9522204a3ab7adfbd8be3e7348
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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