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

HRID 867043Notes

Reaction equation

HRID 867043 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-8c468f1ba5c0446ca231e3956d5433c2
Source dataset
uspto-grants-1978_07
Patent number
US04102669

Reaction notes

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