Hydrochloric Acid → 2-Benzylpiperidine hydrochloride

HRID 1955039Notes

Reaction equation

HRID 1955039 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:14].CCO>CO>[ClH:14].[CH2:1]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 75812-(Phenylmethyl)pyridine

Product 1

HCID 173898172-Benzylpiperidine hydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-benzylpyridine (2.0 g, 12 mmol) in MeOH (50 mL) containing conc. HCl (1 mL) was hydrogenated in a Parr apparatus over Pt (PtO2, 30 mg) at 25° C. The reaction was allowed to proceed at 22 psi for 5 h, 45 psi for 4 h, then overnight at 22 to 12 psi. The catalyst was removed by filtration and the solvent was removed in vacuo to give a syrup. Absolute EtOH (50 mL) was added and then evaporated in vacuo. This was repeated to give a near colorless solid. The solid was triturated with ether (2×20 mL) and dried in vacuo to give a colorless powder (2.36 g, 94% yield); mp 128-131° C., lit. 125-130° C. (vide supra); 1H NMR (D2O) 1.45-2.05 (m, 6H), 2.80-3.05 (m, 3H), 3.27-3.45 (m, 2H) 7.26-7.46 (m, 5H).

Workup

  1. wait45 psi for 4 h
  2. customovernight
  3. customThe catalyst was removed by filtration
  4. customthe solvent was removed in vacuo
  5. customto give a syrup
  6. customevaporated in vacuo
  7. customto give a near colorless solid
  8. customThe solid was triturated with ether (2×20 mL)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-b4e3d91c16834ceba72e87def7fcb52e
Source dataset
uspto-grants-2000_09
Patent number
US06124317

Reaction notes

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