Potassium Hydroxide → 4-Piperidinone, 3,5-bis[[4-(diethylamino)phenyl]methylene]-1-methyl-

HRID 1649194Notes

Reaction equation

HRID 1649194 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[CH2:9]([N:11]([CH2:20][CH3:21])[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)[CH3:10].[OH-].[K+]>CO>[CH2:9]([N:11]([CH2:20][CH3:21])[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[C:4]2[C:5](=[O:8])[C:6](=[CH:16][C:15]3[CH:18]=[CH:19][C:12]([N:11]([CH2:9][CH3:10])[CH2:20][CH3:21])=[CH:13][CH:14]=3)[CH2:7][N:2]([CH3:1])[CH2:3]2)=[CH:14][CH:13]=1)[CH3:10]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 671144-(Diethylamino)benzaldehydeHCID 740491-Methyl-4-piperidone

Product 1

HCID 43722274-Piperidinone, 3,5-bis[[4-(diethylamino)phenyl]methylene]-1-methyl-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-methyl-4-piperidone (2.25 g) and 7.1 g of p-diethylamino-benzaldehyde were added to a solution of 4 g potassium hydroxide in 50 ml methanol. The reaction mixture was heated at reflex 31/2 hours and allowed to stand at room temperature overnight. The product was collected and recrystallized from 700 ml acetonitrile. The UV spectra of the isolated product was consistent with the structure of the titled compound.

Workup

  1. temperatureThe reaction mixture was heated at reflex 31/2 hours
  2. customThe product was collected
  3. customrecrystallized from 700 ml acetonitrile

Sources & evidence

ORD record
ord-18f8c52490b740cd9b5c4b3e7baa281d
Source dataset
uspto-grants-1983_11
Patent number
US04415621

Reaction notes

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