Sodium Hydroxide → Sodium 1-benzylpiperidine-4-carboxylate

HRID 2274485Notes

Reaction equation

HRID 2274485 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+:20]>C(O)C>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]([O-:16])=[O:15])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[Na+:20]

Participants

4

Reactant 2

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

Product 1

HCID 67360726Sodium 1-benzylpiperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution consisting of ethyl 1-benzylpiperidine-4-carboxylate (500 mg, 2.02 mmol) in ethanol (10 mL) was added 1 N sodium hydroxide (2.02 mL, 2.02 mmol) and the reaction mixture was stirred at room temperature overnight. Most of the ethanol was removed under reduced pressure and stirring was continued for six hours. Toluene was added to remove most of the water by azeotrope and the material was dried under high vacuum overnight to provide the title intermediate as a white solid.

Workup

  1. customMost of the ethanol was removed under reduced pressure
  2. stirringstirring
  3. waitwas continued for six hours
  4. additionToluene was added
  5. customto remove most of the water by azeotrope
  6. customthe material was dried under high vacuum overnight

Sources & evidence

ORD record
ord-623fa6dc7a264c3fb8ebbf9e90bdd645
Source dataset
uspto-grants-2015_09
Patent number
US09126973B2

Reaction notes

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