Sodium Hydroxide → 4-(3-(2-oxo-1,8-naphthyridin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylic acid

HRID 385644Notes

Reaction equation

HRID 385644 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:12][CH2:13][CH2:14][C:15]1([C:29]([O:31]CC)=[O:30])[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][S:23][C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH2:17][CH2:16]1.[OH-].[Na+]>C(O)C>[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:12][CH2:13][CH2:14][C:15]1([C:29]([OH:31])=[O:30])[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][S:23][C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 57815357ethyl 4-(3-(2-oxo-1,8-naphthyridin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate

Product 1

HCID 578152484-(3-(2-oxo-1,8-naphthyridin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylic acidYield 77.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.30 g of ethyl 4-(3-(2-oxo-1,8-naphthyridin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate in 5 mL of ethanol, 1.7 mL of a 20% aqueous sodium hydroxide solution was added at room temperature, and the mixture was heated under reflux while stirring for 7 hours. Thereto was further added 0.3 mL of a 20% aqueous sodium hydroxide solution, and mixture was stirred for 1 hour, and then cooled to room temperature, and the solvent was distilled off under reduced pressure. The resultant residue was charged with water and adjusted to pH 6.5 with 1 mol/L hydrochloric acid. The solid was filtered off to obtain 0.22 g of 4-(3-(2-oxo-1,8-naphthyridin-1(2H)-yl) propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylic acid as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. stirringwas stirred for 1 hour
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe resultant residue was charged with water
  6. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-779986f71f28492ba8cec07ccd59676d
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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