Hydrochloric Acid → 1-(3-Methoxy-benzyl)-piperidine-2-carboxylic acid

HRID 1741401Notes

Reaction equation

HRID 1741401 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[C:13]([O:15]CC)=[O:14].[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18367365HCID 18367365, compound

Product 1

HCID 32970831-(3-Methoxy-benzyl)-piperidine-2-carboxylic acidYield 97.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 1-(3-methoxybenzyl)-2-piperidinecarboxylate (3.0 g) and 1N NaOH (21.6 ml) in ethanol (31.6 ml) was stirred at 70° C. overnight. The reaction mixture was cooled to room temperature, acidified with 1N hydrochloric acid, and evaporated in vacuo. The residue was extracted with methylene chloride and the extract was evaporated in vacuo to afford 1-(3-methoxybenzyl)-2-piperidinecarboxylic acid (2.64 g) as an amorphous powder. (+) APCI-MS (m/z): 250 (M+ +1) mp: 186.0-187.3° C. IR (Film): 1600, 1265 cm-1NMR (CDCl3, δ): 1.3-1.85 (6H, m), 2.2-2.3 (1H, m), 2.86-2.93 (1H, m), 3.09 (1H, dd, J=7.6, 4.3 Hz), 3.52 (1H, d, J=13.4 Hz), 3.74 (3H, s), 3.87 (1H, d, J=13.4 Hz), 6.81-6.93 (3H, m), 7.24 (1H, d, J=8.0 Hz)

Workup

  1. customevaporated in vacuo
  2. extractionThe residue was extracted with methylene chloride
  3. customthe extract was evaporated in vacuo

Sources & evidence

ORD record
ord-fb9fd6884af849a781586387b769962c
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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