Sodium Hydroxide → (1-Acetylpiperidin-4-yl)acetic acid

HRID 126857Notes

Reaction equation

HRID 126857 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][C:11]([O:13]CC)=[O:12])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][C:11]([OH:13])=[O:12])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54363171Ethyl 1-acetyl-4-piperidineacetate

Product 1

HCID 10442408(1-Acetylpiperidin-4-yl)acetic acidYield 36.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 92 parts of ethyl 1-acetyl-4-piperidineacetate in 200 parts of ethanol are added dropwise (slowly) 65 parts of sodium hydroxide solution 30%. Upon completion, stirring is continued for 2 hours in a warm water-bath. The reaction mixture is poured onto water and the whole is filtered over hyflo. The clear filtrate is concentrated to a third of its volume and the concentrate is acidified with a diluted hydrochloric acid solution. While cooling, the product is allowed to crystallize. It is filtered off and dried, yielding 29 parts (36.5%) of 1-acetyl-4-piperidineacetic acid; mp. 124.1° C.

Workup

  1. additionThe reaction mixture is poured onto water
  2. filtrationthe whole is filtered over hyflo
  3. concentrationThe clear filtrate is concentrated to a third of its volume
  4. temperatureWhile cooling
  5. customto crystallize
  6. filtrationIt is filtered off
  7. customdried

Sources & evidence

ORD record
ord-d56d45b94ed74a0d8f100f148fb2db11
Source dataset
uspto-grants-1981_03
Patent number
US04254127

Reaction notes

Loading…