Phenylacetonitrile → alpha-(1-(Phenylmethyl)piperidin-4-ylidene)phenylacetonitrile

HRID 1018545Notes

Reaction equation

HRID 1018545 reaction equation
[O-]CC.[Na+].[CH2:5]([C:12]#[N:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:14]([N:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([N:21]1[CH2:26][CH2:25][C:24](=[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]#[N:13])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 8794PhenylacetonitrileHCID 192201-Benzyl-4-piperidoneHCID 2723922Sodium ethoxide

Product 1

HCID 111223alpha-(1-(Phenylmethyl)piperidin-4-ylidene)phenylacetonitrile

Procedure

To a solution sodium ethoxide is added benzyl cyanide and N-benzyl-4-piperidone (XI-1) and the reaction is run at 85° C. for 3 h. Workup with concentrated hydrochloric gives the intermediate (1-benzyl-piperidin-4-yl-idene)-phenyl-acetonitrile which is treated with potassium cyanide. Reduction of one carbonyl group is performed with an excess of diisobutylaluminium hydride and elimination is performed with acetic acid. The obtained intermediate N-benzyl protected spiropiperidine is treated with hydrogen and palladium on charcoal. After stirring in a hydrogen atmosphere at room temperature (CF3)2C6H3COCl is added to give a compound of formula I-13.

Workup

  1. concentrationWorkup with concentrated hydrochloric

Sources & evidence

ORD record
ord-435ff125a6a44514900cc6420488fe40
Source dataset
uspto-grants-2002_11
Patent number
US06482829B2

Reaction notes

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