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

HRID 2193177Notes

Reaction equation

HRID 2193177 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-methoxyl-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-dba5425fa45a482aab44daa1eef34007
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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