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

HRID 507846Notes

Reaction equation

HRID 507846 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 60F) 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 60F)

Sources & evidence

ORD record
ord-251ad3f37d6d4db98e50b1c709dd8a43
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

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