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

HRID 462254Notes

Reaction equation

HRID 462254 reaction equation
[ClH:1].[NH: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.Cl>C(O)C>[ClH:1].[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][NH:2][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 30848514-Piperidone hydrochloride

Product 1

HCID 3557494-Piperidinone, 3,5-bis(phenylmethylene)-, hydrochlorideYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 10 g of 4-piperidone, hydrochloride, hydrate and 14 g of benzaldehyde in 50 ml of ethanol is cooled to 10° C and treated dropwise with 25 ml of concentrated hydrochloric acid (temperature maintained at less than 25° C during the addition) and refluxed for 4 hours; the product begins to separate soon after refluxing begins. After standing at room temperature for about 16 hours, the resulting solid is filtered, washed with cold ethanol and with ether, and air-dried yielding 19.4 g of material, melting point 272°-274° C, dec.

Workup

  1. temperaturemaintained at less than 25° C during the addition) and
  2. temperaturerefluxed for 4 hours
  3. customto separate soon
  4. temperatureafter refluxing
  5. filtrationthe resulting solid is filtered
  6. washwashed with cold ethanol and with ether
  7. customair-dried

Sources & evidence

ORD record
ord-2638860426694659ae38256e7d6e47d8
Source dataset
uspto-grants-1977_12
Patent number
US04065617

Reaction notes

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