Ethyl 3-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]-propionate → 3-[4-[(4-Chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]propionic acid

HRID 1651558Notes

Reaction equation

HRID 1651558 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1>[OH-].[Na+].C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH2:12][CH2:11]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 15055865Ethyl 3-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]-propionate

Product 1

HCID 150558663-[4-[(4-Chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]propionic acidYield 92.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

1.00 g (2.48 mmol) of ethyl 3-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]propionate obtained in Example 24 was dissolved in a mixed solution of 1 ml of 50 wt % of aqueous sodium hydroxide and 8 ml of ethanol, and the solution was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, neutralized with dil. hydrochloric acid and then extracted with chloroform. The chloroform extract was dried over anhydrous sodium sulfate and then concentrated to give 0.86 g (92%) of 3-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]propionic acid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with chloroform
  3. extractionThe chloroform extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-87790da58855434a9fdd1f40c701393b
Source dataset
uspto-grants-1990_05
Patent number
US04929618

Reaction notes

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