1-(4-Chlorobenzoyl)-4-(4-cyanobenzylidene)piperidine → 1-(4-Chlorobenzoyl)-4-(4-cyanobenzyl)piperidine

HRID 129082Notes

Reaction equation

HRID 129082 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH2:13][CH2:12][C:11](=[CH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]#[N:22])=[CH:19][CH:20]=3)[CH2:12][CH2:13]2)=[O:7])=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 152313981-(4-Chlorobenzoyl)-4-(4-cyanobenzylidene)piperidine

Product 1

HCID 193727101-(4-Chlorobenzoyl)-4-(4-cyanobenzyl)piperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 1140TolueneSolvent

Procedure

8.4 g of 1-(4-chlorobenzoyl)-4-(4-cyanobenzylidene)piperidine are hydrogenated (5 bar) at ambient temperature for 15 minutes in 400 ml of toluene with the addition of 2 g of palladium black. After addition of 1 g of palladium black, the mixture is hydrogenated for an additional 2.5 hours, a further 1 g of catalyst is added and the mixture is hydrogenated for an additional hour. 7.9 g (93.3% of theory) of the title compound are obtained as a colourless powder of melting point 137°-139° C.

Workup

  1. customat ambient temperature
  2. customfor 15 minutes
  3. waitthe mixture is hydrogenated for an additional hour

Sources & evidence

ORD record
ord-a74b541a920247af92da80551b4f1739
Source dataset
uspto-grants-1995_11
Patent number
US05466687

Reaction notes

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