Nitric Acid → HCID 178474954, compound
Reaction equation
[C:1]([NH2:4])(=[O:3])[CH3:2].[C:5]1([C@H:11]2[CH2:16][CH2:15][C@H:14](N)[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.FC(F)(F)C(O)=O.[N+:25]([O-:28])(O)=[O:26]>>[N+:25]([C:8]1[CH:7]=[CH:6][C:5]([C@H:11]2[CH2:16][CH2:15][C@H:14]([NH:4][C:1](=[O:3])[CH3:2])[CH2:13][CH2:12]2)=[CH:10][CH:9]=1)([O-:28])=[O:26]Participants
Procedure
To an ice-cooled solution of 4.67 g. of trans 4-phenylcyclohexylamine acetamide (obtained as in Example 80) in 25 ml. of trifluoroacetic acid, 9 ml. of nitric acid is added. Following about 4 hours of standing in the cold, the mixture is poured onto ice. The precipitate is extracted with methylene chloride and the organic layer washed with aqueous sodium bicarbonate solution. The organic solution is evaporated to dryness and the residue chromatographed on a 500 ml. column of Florisil, with elution by 2 l. of 20% acetone in Skellysolve B. The higher melting solid fractions recovered are combined and recrystallized from a mixture of methylene chloride and ethyl acetate to give 3.09 g. (54% yield) of crystalline trans N-[4-(p-nitrophenyl)cyclohexyl]acetamide, having a melting point of 221° to 224° C.
Workup
- additionis poured onto ice
- extractionThe precipitate is extracted with methylene chloride
- washthe organic layer washed with aqueous sodium bicarbonate solution
- customThe organic solution is evaporated to dryness
- customthe residue chromatographed on a 500 ml
- washcolumn of Florisil, with elution by 2 l
- customrecovered
- customrecrystallized from a mixture of methylene chloride and ethyl acetate
- customto give 3.09 g
Sources & evidence
- ORD record
- ord-afeb90da8c124622a32954ff0fe639f2
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03960961
Reaction notes
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