Piperidine → Benzyl 4-(piperidin-1-ylmethylene)piperidine-1-carboxylate

HRID 706973Notes

Reaction equation

HRID 706973 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1)=O.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C1(C)C=CC=CC=1>[N:19]1([CH:1]=[C:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:5][CH2:4]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 2776272Benzyl 4-formylpiperidine-1-carboxylate

Product 1

HCID 86642880Benzyl 4-(piperidin-1-ylmethylene)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of benzyl 4-formylpiperidine-1-carboxylate (12.5 g) in toluene (120 mL) was added piperidine (6.46 g). The mixture was stirred at reflux under a Dean-Stark trap overnight. The mixture was then concentrated under vacuum and the residue was used directly in the next step.

Workup

  1. temperatureat reflux under a Dean-Stark trap overnight
  2. concentrationThe mixture was then concentrated under vacuum

Sources & evidence

ORD record
ord-8e03a363b05641e18794e05c6b6d5efd
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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