Hydrochloric Acid → 2-Methyl-2-(1-methylpiperidin-3-yl)propanoic acid

HRID 499708Notes

Reaction equation

HRID 499708 reaction equation
C[O:2][C:3](=[O:14])[C:4]([CH3:13])([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH3:12])[CH2:7]1)[CH3:5].[OH-].[Li+].Cl>CO>[CH3:13][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH3:12])[CH2:7]1)([CH3:5])[C:3]([OH:14])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 668891612-Methyl-2-(1-methyl-piperidin-3(r,s)-yl)-propionic acid methyl ester

Product 1

HCID 668879152-Methyl-2-(1-methylpiperidin-3-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.200 g of 2-methyl-2-(1-methyl-piperidin-3(R,S)-yl)-propionic acid methyl ester are dissolved in 4 ml of methanol. 4 ml of a 1M aqueous lithium hydroxide solution are added and the mixture is stirred for 16 hours at room temperature. The reaction mixture is neutralised with 1M HCl and extracted with ethyl acetate (3×50 ml). The organic phases are combined and concentrated by evaporation. The residue is purified by means of flash chromatography (SiO2 60 F) to provide the title compound as a colourless oil. Rf 0.15 (150:54:10:1 dichloromethane-methanol-acetic acid-water).

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. concentrationconcentrated by evaporation
  3. customThe residue is purified by means of flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-240c917ab8bb4b0e980ff73e278c96b2
Source dataset
uspto-grants-2010_08
Patent number
US07767690B2

Reaction notes

Loading…