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

HRID 462020Notes

Reaction equation

HRID 462020 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=C.[CH2:31]([N:34]1[CH:39]=[C:38]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:48])[F:47])[CH:41]=2)[C:37](=[O:50])[C:36]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[CH:35]1)[CH:32]=[CH2:33].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:31]([N:34]1[CH2:39][CH:38]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:48])([F:47])[F:49])[CH:41]=2)[C:37](=[O:50])[CH:36]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:35]1)[CH:32]=[CH2:33]

Participants

6

Reactant 5

HCID 8025Ethyl formateHCID 82291Allylamine hydrochlorideHCID 1088302-Propanone, 1-phenyl-3-(3-(trifluoromethyl)phenyl)-HCID 128792403-Phenyl-1-(prop-2-en-1-yl)-5-[3-(trifluoromethyl)phenyl]pyridin-4(1H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 203170201-Allyl-3-phenyl-5-(3-trifluoromethylphenyl)-4-piperidinone

Procedure

Twenty g. of 1-phenyl-3-(3-trifluoromethylphenyl)-2-propanone was reacted with ethyl formate and allylamine hydrochloride as described in Examples 1-3 to obtain 10.8 g. of 1-allyl-3-phenyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridinone, which was reacted with 2 g. of lithium aluminum hydride as described in Examples 1-3. The reaction mixture was worked up and chromatographed as described in the examples above to obtain 1.2 g. of the products of Examples 33 and 34 as a mixture. The compounds were identified by mass spectroscopy, which showed an indicated molecular weight of 357. A yield of 1.0 g. of the compound of Example 35 was obtained, which showed a mass spectroscopy molecular weight of 359.

Workup

  1. customto obtain 10.8 g
  2. customchromatographed
  3. customto obtain 1.2 g

Sources & evidence

ORD record
ord-72eae7c7a51c4e6883e38dea8a34a9da
Source dataset
uspto-grants-1977_12
Patent number
US04065290

Reaction notes

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