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

HRID 2083188

Reaction equation

HRID 2083188 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].[CH3:1][N:2]1[CH2:7][C:6](=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5](=[O:8])[C:4](=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3]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. (0.5 mole) of 1-methyl-4-piperidinone and 106.0 g. (1.0 mole) of benzaldehyde in 400 ml. of ethanol is cooled in an ice bath and treated with HCl gas until 250 g. is absorbed. The red-colored solution is allowed to stand at room temperature overnight. The resulting deep red-brown solution is seeded, allowed to stand overnight at room temperature, and the crystalline solid is filtered on a sintered-glass funnel and washed with cold ethanol, followed by ether. After drying in a desiccator, the solid (146 g.) is digested in 400 ml. of hot ethanol (75°), cooled and filtered to give 120 g. of pale yellow product, m.p. 242-244° (dec.).

Workup

  1. customis absorbed
  2. waitto stand overnight at room temperature
  3. filtrationthe crystalline solid is filtered on a sintered-glass funnel
  4. washwashed with cold ethanol
  5. customAfter drying in a desiccator
  6. temperatureof hot ethanol (75°), cooled
  7. filtrationfiltered
  8. customto give 120 g

Sources & evidence

ORD record
ord-f4b108035e4041fe9bea41b7f669e775
Source dataset
uspto-grants-1978_04
Patent number
US04085102

Linked notes

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