Acetic Acid → 1-[2-(4-Chlorophenyl)-4-quinolinyl]-4-piperidinecarboxylic acid

HRID 638261Notes

Reaction equation

HRID 638261 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].C(O)C.C(O)(=O)C>O>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:14]2[CH:13]=[C:12]([N:9]3[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]3)[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 136039061-[2-(4-Chlorophenyl)-4-quinolinyl]-4-piperidinecarboxylic acid ethyl ester

Product 1

HCID 136039071-[2-(4-Chlorophenyl)-4-quinolinyl]-4-piperidinecarboxylic acidYield 100.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.5 g (3.8 mmol) of 1-[2-(4-chlorophenyl)-4-quinolinyl]-4-piperidinecarboxylic acid ethyl ester, 2.7 ml of 3N aqueous sodium hydroxide, and 50 ml of ethanol was heated on a steam bath for 0.5 hr. It was then cooled, acidified with acetic acid, and diluted with water to give 1.4 g of product, mp 245°-247°.

Workup

  1. temperaturewas heated on a steam bath for 0.5 hr
  2. temperatureIt was then cooled

Sources & evidence

ORD record
ord-e3aa70b7e4df4b3dab8329ec19606d95
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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