Ethyl formate → 3-(3-Methoxyphenyl)-1-methyl-5-phenylpiperidin-4-one

HRID 867042Notes

Reaction equation

HRID 867042 reaction equation
COC1C=C(CC(=O)CC2C=CC=CC=2)C=CC=1.C(OCC)=O.Cl.CN.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([C:35]2[C:40](=[O:41])[C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:38][N:37]([CH3:48])[CH:36]=2)[CH:32]=[CH:33][CH:34]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:35]2[C:40](=[O:41])[CH:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:38][N:37]([CH3:48])[CH2:36]2)[CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 5

HCID 8025Ethyl formateHCID 1812344(1H)-Pyridinone, 3-(3-methoxyphenyl)-1-methyl-5-phenyl-HCID 6364545Methylamine hydrochlorideHCID 203170611-(3-Methoxyphenyl)-3-phenylpropan-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 203170953-(3-Methoxyphenyl)-1-methyl-5-phenylpiperidin-4-one

Procedure

A 54 g. portion of 1-(3-methoxyphenyl)-3-phenyl-2-propanone was reacted with ethyl formate and methylamine hydrochloride as described in Examples 1-3 to prepare 10 g. of 3-(3-methoxyphenyl)-1-methyl-5-phenyl-4(1H)-pyridinone, which was reduced with 2 g. of lithium aluminum hydride. The reaction mixture was worked up as in the examples above and chromatographed over a silica gel column. About 1.4 g. of a mixture of the compounds of Examples 24 and 25 was obtained, an oil which was identified by mass spectroscopy as having a molecular weight of 293. About 1.3 g. of the piperidinone of Example 26 was recovered, which had an indicated molecular weight of 295 by mass spectroscopy.

Workup

  1. customto prepare 10 g
  2. customchromatographed over a silica gel column
  3. additionof a mixture of the compounds of Examples 24
  4. custom25 was obtained
  5. customof the piperidinone of Example 26 was recovered

Sources & evidence

ORD record
ord-6224391921884feaa182cf38d4bfcf4b
Source dataset
uspto-grants-1978_07
Patent number
US04102669

Reaction notes

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