Hydrochloric Acid → 1-Benzylpiperidine-3-carboxylic acid

HRID 1269743Notes

Reaction equation

HRID 1269743 reaction equation
[OH-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([O:18]CC)=[O:17])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>O1CCCC1.O1CCOCC1>[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([OH:18])=[O:17])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 2736370ethyl 1-benzylpiperidine-3-carboxylate

Product 1

HCID 162440101-Benzylpiperidine-3-carboxylic acidYield 101.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

A 4N-aqueous sodium hydroxide solution (15 ml) was added to a solution of ethyl 1-benzyl-3-piperidinecarboxylate (7.00 g, 28.3 mmol) in a mixture of tetrahydrofuran (30 ml) and 1,4-dioxane (30 ml), and the resulting mixture was stirred at room temperature for 4 hours. After a 4N-aqueous sodium hydroxide solution (15 ml) was added again, the resulting mixture was stirred overnight at room temperature. After completion of the reaction, the reaction solution was neutralized by the addition of 2N-hydrochloric acid (15 ml) under ice-cooling and the resulting mixture was subjected to azeotropic concentration with toluene. The residue was suspended in ethanol, followed by filtration, and the filtrate was concentrated to obtain 1-benzyl-3-piperidinecarboxylic acid (6.3 g, 100%).

Workup

  1. stirringthe resulting mixture was stirred overnight at room temperature
  2. customAfter completion of the reaction
  3. temperaturecooling
  4. concentrationthe resulting mixture was subjected to azeotropic concentration with toluene
  5. filtrationfollowed by filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c75b1278771e4d14a9bc4b78482a7a52
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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