Sodium Hydroxide → HCID 59397925, compound

HRID 39846Notes

Reaction equation

HRID 39846 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:36])[N:10]2[CH2:13][CH2:14][CH2:15][C:16]2([C:31]([O:33]CC)=[O:32])[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:18][CH2:17]2)=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:36])[N:10]2[CH2:13][CH2:14][CH2:15][C:16]2([C:31]([OH:33])=[O:32])[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][O:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:20][CH2:21]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59398185Ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinolin-1-yl)propyl)-1-(2-phenoxyethyl)piperidine-4-carboxylate

Product 1

HCID 59397925HCID 59397925, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1.5 mL of an ethanol solution containing 0.12 g of ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinolin-1-yl)propyl)-1-(2-phenoxyethyl)piperidine-4-carboxylate, 0.7 mL of 20% aqueous sodium hydroxide solution was added at room temperature and refluxed with heating for 4.5 hours. After the reaction mixture was cooled to the room temperature, the solvent was removed under reduced pressure, water was added, adjusted to pH 6.5 with 6.0 mol/L hydrochloric acid. The resulting solid was filtered to give 87 mg of 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinolin-1-yl)propyl)-1-(2-phenoxyethyl)piperidine-4-carboxylic acid as a pale yellow solid.

Workup

  1. additionwas added at room temperature
  2. temperaturerefluxed
  3. temperaturewith heating for 4.5 hours
  4. customthe solvent was removed under reduced pressure, water
  5. additionwas added
  6. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-a34a104d660243d2aa746965483b6844
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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