Benzaldehyde → 4-Piperidinone, 1-methyl-3,5-bis(phenylmethylene)-, hydrochloride

HRID 462252

Reaction equation

HRID 462252 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[ClH:17]>C(O)C>[ClH:17].[CH:9](=[C:4]1[C:5](=[O:8])[C:6](=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][N:2]([CH3:1])[CH2:3]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 740491-Methyl-4-piperidone

Product 1

HCID 3587084-Piperidinone, 1-methyl-3,5-bis(phenylmethylene)-, hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 57.0 g of 1-methyl-4-piperidone and 106.0 g of benzaldehyde in 400 ml of ethanol is cooled in an ice-bath and treated with hydrogen chloride gas until 250 g is absorbed. The solution is allowed to stand at room temperature for about 16 hours. The resulting solution is seeded, allowed to stand for about 16 hours at room temperature and the crystalline solid filtered on a sintered-glass funnel and washed with cold ethanol and then with ether. After drying in a desiccator, the solid (146 g) is digested in 400 ml of hot ethanol, cooled and filtered to give 120 g of product, melting point 242°-244° C, dec. Recrystallization of 11 g of this material from 35 ml of dimethylformamide gives 9.2 g of product, melting point 242°-244° C, dec.

Workup

  1. customis absorbed
  2. waitto stand for about 16 hours at room temperature
  3. filtrationthe crystalline solid filtered on a sintered-glass funnel
  4. washwashed with cold ethanol
  5. customAfter drying in a desiccator
  6. temperaturecooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-c503de4aa7884a33a74ca95625370b3b
Source dataset
uspto-grants-1977_12
Patent number
US04065617

Linked notes

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