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

HRID 132835

Reaction equation

HRID 132835 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.O>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 51700761-Benzyl-2-piperidone

Product 1

HCID 117468121-Benzyl-4-(1-pyrrolidinyl)-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-benzyl piperidone (20.0 g, 53 mmol) and pyrrolidine (14.0 mL, 80 mmol) in 300 mL of toluene was warmed at reflux overnight with azeotropic removal of water. The reaction mixture was then cooled and concentrated under reduced pressure. The resultant dark oil was dissolved in 200 mL of ether, dried over magnesium sulfate, filtered and concentrated under reduced pressure.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resultant dark oil was dissolved in 200 mL of ether
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-36247de45a004927a91ccba647c91237
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Linked notes

Loading…