Ethyl formate → 1-Ethyl-3-phenyl-5-(3-trifluoromethylphenyl)-4-piperidinone

HRID 462019Notes

Reaction equation

HRID 462019 reaction equation
C1(CC(=O)CC2C=CC=C(C(F)(F)F)C=2)C=CC=CC=1.C(OCC)=O.Cl.C(N)C.[CH2:30]([N:32]1[CH:37]=[C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=2)[C:35](=[O:48])[C:34]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[CH:33]1)[CH3:31].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:30]([N:32]1[CH2:37][CH:36]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:45])[F:46])[CH:39]=2)[C:35](=[O:48])[CH:34]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:33]1)[CH3:31]

Participants

6

Reactant 5

HCID 8025Ethyl formateHCID 11198Ethylamine hydrochlorideHCID 1088302-Propanone, 1-phenyl-3-(3-(trifluoromethyl)phenyl)-HCID 128792811-Ethyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]pyridin-4(1H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 203169951-Ethyl-3-phenyl-5-(3-trifluoromethylphenyl)-4-piperidinone

Procedure

An 11.5 g. portion of 1-phenyl-3-(3-trifluoromethylphenyl)-2-propanone was reacted with ethyl formate and ethylamine hydrochloride as described in Examples 1-3 to produce 6.8 g. of 1-ethyl-3-phenyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridinone, which was reduced with 2 g. of lithium aluminum hydride as described above. After column chromatography as described in the examples above, the products of Examples 27 and 28 were recovered as a mixture. Mass spectroscopy of the mixture showed a molecular weight of 345, and the yield was 1.2 g. The molecular weight of the product of Example 29 was indicated as 347 by mass spectroscopy, yield 1.9 g.

Workup

  1. customto produce 6.8 g
  2. customwere recovered as a mixture

Sources & evidence

ORD record
ord-0ce3678c397b43cba116b58c7ceb0665
Source dataset
uspto-grants-1977_12
Patent number
US04065290

Reaction notes

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