Sodium Hydroxide → 1-Methylpiperidine-4-carboxylic acid

HRID 1374592Notes

Reaction equation

HRID 1374592 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]([O:12]CC)=[O:11])[CH2:6][CH2:5]1>C(O)C>[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11062856Ethyl 1-methylpiperidine-4-carboxylate

Product 1

HCID 27369391-Methylpiperidine-4-carboxylic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.5 cm3 of a 4 N aqueous sodium hydroxide solution are added, at 20° C., to 7.60 g of ethyl 1-methyl-4-piperidinecarboxylate in solution in 35 cm3 of ethanol. After stirring for 20 hours, the reaction mixture is concentrated to a reduced volume and then neutralized with 12.5 cm3 of a 4 N aqueous hydrochloric acid solution and finally concentrated to dryness under reduced pressure (2.7 kPa). The residue is stirred in 60 cm3 of anhydrous ethanol, and then filtered. The filtrate is concentrated to dryness under reduced pressure (2.7 Kpa) at 20° C., to give 6.3 g of 1-methyl-4-piperidinecarboxylic acid in the form of a white solid.

Workup

  1. concentrationthe reaction mixture is concentrated to a reduced volume
  2. concentrationfinally concentrated to dryness under reduced pressure (2.7 kPa)
  3. stirringThe residue is stirred in 60 cm3 of anhydrous ethanol
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated to dryness under reduced pressure (2.7 Kpa) at 20° C.

Sources & evidence

ORD record
ord-2c09fabce48341da8778a232f299a4c6
Source dataset
uspto-grants-2007_01
Patent number
US07166594B2

Reaction notes

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