Sodium Hydroxide → 1-Benzylpiperidine-4-carboxylic acid

HRID 1291186Notes

Reaction equation

HRID 1291186 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16]CC)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1.O>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 90423Ethyl 1-benzylpiperidine-4-carboxylate

Product 1

HCID 47149831-Benzylpiperidine-4-carboxylic acidYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

0.8 g (0.00323 mol) of ethyl 1-benzylpiperidine-4-carboxylate was dissolved in a mixture of 5 ml of dioxan, 2 ml of water and 3.5 ml (0.0035 mol) of 1N aqueous NaOH. After stirring for 15 min. 3.5 ml (0.0035 mol) of 1N aqueous HCI were added, the mixture was diluted with 20 ml of water, the dioxan was removed by distillation and the residue which remained was lyophilized. The residue was boiled twice with 100 ml of isopropanol each time and the combined organic phases were filtered and concentrated. The product crystallized out in the cold. 0.586 g (83%) of 1-benzylpiperidine-4-carboxylic acid was obtained as white crystals; m.p. 167°-168°.

Workup

  1. addition3.5 ml (0.0035 mol) of 1N aqueous HCI were added
  2. customthe dioxan was removed by distillation
  3. filtrationthe combined organic phases were filtered
  4. concentrationconcentrated
  5. customThe product crystallized out in the cold

Sources & evidence

ORD record
ord-01127f7dac544b5f8ac746ad3ea55b70
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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