Hydrochloric Acid → 3-Benzylpiperidine hydrochloride

HRID 324537

Reaction equation

HRID 324537 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:14]>CO.O=[Pt]=O>[ClH:14].[CH2:1]([CH:8]1[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 121123-Benzylpyridine

Product 1

HCID 161878763-Benzylpiperidine hydrochlorideYield 68%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-benzylpyridine (10 g, 59.8 mmol) in methanol (150 mL) were added PtO2(350 mg) and HCl conc. (5 mL). This heterogeneous solution was hydrogenated in a Parr hydrogenator at 20-25psi at 25° C. and for 24 hrs then filtered through a celite pad and concentrated in vacuum. The crude compound was purified by crystallization from acetone/diethyl ether to give a white solid (8.5 g, 68%). 1H-NMR (DMSO): 1.05-1.2 (m, 1H); 1.5-1.75 (m, 3H); 1.87-2.05 (m, 1H); 2.4-2.55 (m, 3H); 2.57-2.75 (m, 1H); 2.982 (d, J=11.7, 1H); 3.97 (d, J=12.0, 1H); 7.136 (d, J=7.0, 2H); 7.184 (d, J=7.0, 1H), 7.296 (t, J=7.2, 2H); 8.89 (bs, 1H); 9.15 (bs, 1H).

Workup

  1. filtrationthen filtered through a celite pad
  2. concentrationconcentrated in vacuum
  3. customThe crude compound was purified by crystallization from acetone/diethyl ether

Sources & evidence

ORD record
ord-f7aa60512dad44b7a0e2e2b4e7a36986
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Linked notes

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