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

HRID 39766Notes

Reaction equation

HRID 39766 reaction equation
C(O)C.[CH3:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([CH3:39])=[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]([C:10]([CH3:39])=[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 HydroxideHCID 59398235HCID 59398235, compound

Product 1

HCID 159855064-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylic acidYield 88.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1 mL of an ethanol solution containing 0.25 g of ethyl 4-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate, 1 mL of 5 mol/L aqueous sodium hydroxide solution was added and stirred under reflux with heating for 5 hours. 2 mL of water was added, removed ethanol under reduced pressure, adjusted to pH 6.0 with 6 mol/L hydrochloric acid, and the resulting solid was filtered to afford 0.21 g of 4-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylic acid as a pale yellow solid.

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. temperaturewith heating for 5 hours
  4. customremoved ethanol under reduced pressure
  5. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-b6ac082c4beb47bcab49ac467f71301d
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

Loading…