Acetic Acid → 2-(2-Piperidinylidene)-acetophenone

HRID 66169Notes

Reaction equation

HRID 66169 reaction equation
[C:1]1([C:7](=[O:18])[C:8](=[C:12]2[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]2)C(=O)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].C(O)(=O)C>C(O)C>[NH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][C:12]1=[CH:8][C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5360545SodiumHCID 1784679721-phenyl-2-piperidin-2-ylidenebutane-1,3-dione

Product 1

HCID 705741542-(2-Piperidinylidene)-acetophenone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.15 g (0.05 mole) of 1-phenyl-2-(2-piperidinylidene)-1,3-butanedione are introduced into a prepared solution of 3.5 g of sodium in 120 ml of ethanol. The reaction mixture is then refluxed for 40 minutes. After cooling, it is neutralised with glacial acetic acid, and filtered off from the sodium acetate. The filtrate is concentrated in the rotary evaporator, and the residue is dissolved in methylene chloride. The solution is repeatedly extracted with water; the organic phase is dried over sodium sulphate, and the solvent is evaporated off in the rotary evaporator. The oily residue is crystallised from ether/hexane to yield 2-(2-piperidinylidene)-acetophenone, m.p. 59°-60°.

Workup

  1. temperatureThe reaction mixture is then refluxed for 40 minutes
  2. temperatureAfter cooling
  3. filtrationfiltered off from the sodium acetate
  4. concentrationThe filtrate is concentrated in the rotary evaporator
  5. dissolutionthe residue is dissolved in methylene chloride
  6. extractionThe solution is repeatedly extracted with water
  7. dry with materialthe organic phase is dried over sodium sulphate
  8. customthe solvent is evaporated off in the rotary evaporator
  9. customThe oily residue is crystallised from ether/hexane

Sources & evidence

ORD record
ord-782b83a1eb9145c18cb4b0943f8389ce
Source dataset
uspto-grants-1978_12
Patent number
US04130652

Reaction notes

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