Sodium Hydroxide → HCID 59398290, compound

HRID 39795Notes

Reaction equation

HRID 39795 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][CH2:24][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][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:21]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59397967ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(3-phenylpropyl)piperidine-4-carboxylate

Product 1

HCID 59398290HCID 59398290, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 0.8 mL of an ethanol solution containing 80 mg of ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(3-phenylpropyl)piperidine-4-carboxylate, 0.2 mL of 20% aqueous sodium hydroxide solution was added and refluxed with heating for 5 hours. After the reaction mixture was cooled to the room temperature, the solvent was removed under reduced pressure, water was added, and adjusted to pH 6.8 with 6.0 mol/L hydrochloric acid. The solvent was removed under reduced pressure, and the residue thus obtained was purified by reversed-phase silica gel column chromatography [eluent; acetonitrile:water=3:7] to give 23 mg of 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(3-phenylpropyl)piperidine-4-carboxylic acid as a white solid.

Workup

  1. additionwas added
  2. temperaturerefluxed
  3. temperaturewith heating for 5 hours
  4. customthe solvent was removed under reduced pressure, water
  5. additionwas added
  6. customThe solvent was removed under reduced pressure
  7. customthe residue thus obtained
  8. customwas purified by reversed-phase silica gel column chromatography [eluent; acetonitrile:water=3:7]

Sources & evidence

ORD record
ord-61fa375f994c46e0b7fe62df0eb7eb6b
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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