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

HRID 704309Notes

Reaction equation

HRID 704309 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[CH2:9]([N:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)[CH2:12][CH3:13])[CH3:10].[OH-].[Na+]>CO>[CH2:9]([N:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[C:6]2[CH2:7][N:2]([CH3:1])[CH2:3][C:4](=[CH:18][C:17]3[CH:20]=[CH:21][C:14]([N:11]([CH2:9][CH3:10])[CH2:12][CH3:13])=[CH:15][CH:16]=3)[C:5]2=[O:8])=[CH:16][CH:15]=1)[CH2:12][CH3:13])[CH3:10]

Participants

5

Reactant 3

HCID 14798Sodium 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

Two grams (17.7 mmoles) of N-methyl-4-piperidone and 6.26 g (35.4 mmoles) of p-N,N-diethylaminobenzaldehyde were introduced into a 100 ml eggplant type flask, to which was added a solution of 0.5 g of sodium hydroxide in 50 ml methanol. The contents of the flask equipped with a reflux condenser were heated under reflux for about one hour with stirring by means of a magnetic stirrer. After allowing the reaction mixture to cool, the deposited organge-colored crystalline product was collected by filtration and thoroughly washed with methanol. Then, it was purified by recrystallization from benzene/chloroform.

Workup

  1. customThe contents of the flask equipped with a reflux condenser
  2. temperaturewere heated
  3. temperatureunder reflux for about one hour
  4. temperatureto cool
  5. filtrationthe deposited organge-colored crystalline product was collected by filtration
  6. washthoroughly washed with methanol
  7. customThen, it was purified by recrystallization from benzene/chloroform

Sources & evidence

ORD record
ord-5e1e128278834561ac839d8f332931cc
Source dataset
uspto-grants-1991_01
Patent number
US04987057

Reaction notes

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