Sodium Hydroxide → 1-Benzylpiperidine-3-carboxylic acid

HRID 10360Notes

Reaction equation

HRID 10360 reaction equation
C([O:8][C:9]([CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:12]1)=[O:10])C1C=CC=CC=1.[OH-].[Na+]>CO>[CH2:17]([N:13]1[CH2:14][CH2:15][CH2:16][CH:11]([C:9]([OH:10])=[O:8])[CH2:12]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 210411401-Benzylpiperidine-3-carboxylic acid benzyl ester

Product 1

HCID 162440101-Benzylpiperidine-3-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution 3.0 g (9.7 mmol) of 1-benzylpiperidine-3-carboxylic acid benzyl ester (Example A21) in methanol (20 mL) was added 1N sodium hydroxide (20 mL), and the reaction is stirred at room temperature for 18 hours. The methanol is removed in vacuo and the basic aqueous solution is acidified to pH 4 with 1.0 M hydrochloric acid. After washing with ethyl acetate, the aqueous acid layer is lyophilized. The solid is suspended in methanol (10 mL), stirred for 10 minutes and filtered. The filtrate is evaporated in vacuo to afford the title compound (2.0 g). 1H NMR (200 MHz, DMSO-d6): δ 7.38–7.23 (m, 5H), 3.58 (s, 2H), 2.98–2.40 (m, 3H), 2.30–1.25 (m, 6H).

Workup

  1. customThe methanol is removed in vacuo
  2. washAfter washing with ethyl acetate
  3. stirringstirred for 10 minutes
  4. filtrationfiltered
  5. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-97eef82bec22448db417033565e432c7
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Reaction notes

Loading…