Potassium Hydroxide → (4-Benzylpiperidin-1-yl)oxoacetic acid

HRID 900801Notes

Reaction equation

HRID 900801 reaction equation
C([O:3][C:4](=[O:20])[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:6])C.[OH-].[K+]>CO>[CH2:13]([CH:10]1[CH2:9][CH2:8][N:7]([C:5](=[O:6])[C:4]([OH:20])=[O:3])[CH2:12][CH2:11]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 3912049HCID 3912049, compound

Product 1

HCID 16110264(4-Benzylpiperidin-1-yl)oxoacetic acidYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 15.5 g (56 mmol) of (4-benzylpiperidin-1-yl)oxoacetic acid ethyl ester, 5 g (79.4 mmol) of potassium hydroxide and 250 ml of methanol is stirred at room temperature for 6 h. Then reaction mixture is concentrated, the residue is taken up in water, acidified with 1N hydrochloric acid, the precipitated product is filtered off, washed with water and dried to yield 11.95 g (85%) of the title compound. Mp.: 115° C. (water).

Workup

  1. customThen reaction mixture
  2. concentrationis concentrated
  3. filtrationthe precipitated product is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2790d32c9a034644a2698a90bba1054f
Source dataset
uspto-grants-2008_04
Patent number
US07361670B2

Reaction notes

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