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

HRID 1043822Notes

Reaction equation

HRID 1043822 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][CH:12]=[C:11]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:10][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 containing N-benzyl piperidone 1 (5 g, 26.4 mmol) and pyrrolidine 2 (2.82 g, 39.6 mmol) in toluene (60 mL) was heated to reflux with azeotropic removal of water. The reaction mixture was then cooled and concentrated under reduced pressure. The resulting oil was dissolved in ether, dried over magnesium sulfate, and concentrated under reduced pressure. The crude enamine 3 was used in the next step.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was then cooled
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting oil was dissolved in ether
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-42a460a4c71d43ed88e133af28773169
Source dataset
uspto-grants-2013_10
Patent number
US08563566B2

Reaction notes

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