1-Benzyl-4-piperidone → 1-Benzyl-4-(1-pyrrolidinyl)-1,2,3,6-tetrahydropyridine

HRID 586703Notes

Reaction equation

HRID 586703 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]([N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1(C)C=CC=CC=1>[CH2:6]([N:13]1[CH2:14][CH:15]=[C:16]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:17][CH2:18]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 192201-Benzyl-4-piperidoneHCID 31268Pyrrolidine

Product 1

HCID 117468121-Benzyl-4-(1-pyrrolidinyl)-1,2,3,6-tetrahydropyridineYield 102%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Pyrrolidine (31.8 mL, 0.38 mol) was added to a solution of 1-benzyl-4-piperidinone (48.0 g, 0.25 mol) in toluene (180 mL) and the mixture refluxed under Dean-Stark conditions for 4.5 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to give the title compound as an orange oil (61.8 g, 100%).

Workup

  1. temperaturethe mixture refluxed under Dean-Stark conditions for 4.5 hours
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d7a90af37cf447299565b82df1e22cb
Source dataset
uspto-grants-2005_08
Patent number
US06936619B2

Reaction notes

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