Sodium Hydroxide → 1-(2-((3-fluorophenyl)thio)ethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylic acid

HRID 39805Notes

Reaction equation

HRID 39805 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]([CH2:22][CH2:23][CH2:24][N:25]3[C:34]4[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=4)[CH:28]=[CH:27][C:26]3=[O:37])([C:17]([O:19]CC)=[O:18])[CH2:13][CH2:12]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][C:14]([CH2:22][CH2:23][CH2:24][N:25]3[C:34]4[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=4)[CH:28]=[CH:27][C:26]3=[O:37])([C:17]([OH:19])=[O:18])[CH2:15][CH2:16]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59398133ethyl 1-(2-((3-fluorophenyl)thio)ethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

Product 1

HCID 593981081-(2-((3-fluorophenyl)thio)ethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylic acidYield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1.5 mL of an ethanol solution containing 90 mg of ethyl 1-(2-((3-fluorophenyl)thio)ethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate, 0.50 mL of 20% aqueous sodium hydroxide solution was added and refluxed with heating for 3.5 hours. After the reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure, water was added, and adjusted to pH 6.5 with 6.0 mol/L hydrochloric acid. The resulting solid was filtered to give 64 mg of 1-(2-((3-fluorophenyl)thio)ethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylic acid as a pale yellow solid.

Workup

  1. additionwas added
  2. temperaturerefluxed
  3. temperaturewith heating for 3.5 hours
  4. customthe solvent was removed under reduced pressure, water
  5. additionwas added
  6. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-7d93ec50d24f4cc0849ca6a2bfa19ab9
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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