Benzoylacetone → 1-phenyl-2-piperidin-2-ylidenebutane-1,3-dione

HRID 66168

Reaction equation

HRID 66168 reaction equation
C(O[C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]=1)C.[C:10]1([C:16](=[O:21])[CH2:17][C:18](=[O:20])[CH3:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([C:16](=[O:21])[C:17](=[C:4]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:5]2)[C:18](=[O:20])[CH3:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 7166BenzoylacetoneHCID 122102552-Ethoxy-3,4,5,6-tetrahydropyridine

Product 1

HCID 1784679721-phenyl-2-piperidin-2-ylidenebutane-1,3-dione

Procedure

12.7 g (0.1 mole) of 2-ethoxy-3,4,5,6-tetrahydropyridine and 24.4 g (0.15 mole) of 1-phenyl-1,3-butanedione are mixed and heated together in a nitrogen atmosphere, with stirring, for 32 hours in an oil bath at 100°. The reaction mixture is cooled, and subsequently chromatographed on silica gel with an ethyl acetate/hexane mixture as the eluant. The main fractions are combined and crystallised from ether to obtain 1-phenyl-2-(2-piperidinylidene)-1,3-butanedione in the form of yellow crystals, m.p. 80°-81°.

Workup

  1. temperatureheated together in a nitrogen atmosphere
  2. temperatureThe reaction mixture is cooled
  3. customsubsequently chromatographed on silica gel with an ethyl acetate/hexane mixture as the eluant
  4. customcrystallised from ether

Sources & evidence

ORD record
ord-b80ae327a1504a2aa6409de3523f995e
Source dataset
uspto-grants-1978_12
Patent number
US04130652

Linked notes

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