Benzaldehyde → HCID 85838726, compound

HRID 462256Notes

Reaction equation

HRID 462256 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[ClH:20]>C(O)C>[ClH:20].[CH:12](=[C:7]1[C:8](=[O:11])[C:9](=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 899951-Butyl-4-piperidone

Product 1

HCID 85838726HCID 85838726, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 31 g of 1-butyl-4-piperidone and 64 g of benzaldehyde in 300 ml of ethanol is cooled to 15° C, treated dropwise with 66 ml of concentrated hydrochloric acid, refluxed for 5 hours, and maintained for about 16 hours at room temperature. The bulk of ethanol is evaporated and the syrupy residue is cooled, diluted to 600 ml with water, treated with 300 ml of ether, stirred, and rubbed; a solid gradually separates. After cooling for several hours, the solid is filtered, washed with ether, and air-dried; yielding 36.7 g of material, melting point 203°-205° C. Following crystallization from 100 ml of dimethylformamide, the material weighs 24.2 g; melting point 212°-214° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. customThe bulk of ethanol is evaporated
  3. temperaturethe syrupy residue is cooled
  4. additiondiluted to 600 ml with water
  5. additiontreated with 300 ml of ether
  6. temperatureAfter cooling for several hours
  7. filtrationthe solid is filtered
  8. washwashed with ether
  9. customair-dried

Sources & evidence

ORD record
ord-22532baebf6945b18ac719949838b22d
Source dataset
uspto-grants-1977_12
Patent number
US04065617

Reaction notes

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