P(Cl)(Cl)(Cl)=O.[NH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=O.[C:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([NH2:30])=[CH:25][C:24]=2[CH3:31])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:13]([C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([N:30]=[C:7]3[CH2:8][CH2:9][CH2:10][CH2:11][NH:6]3)=[CH:25][C:24]=2[CH3:31])=[CH:21][CH:22]=1)([CH3:16])([CH3:15])[CH3:14]A solution of 0.2 g (1.5 mmol) of phosphoric trichloride in 5 ml toluene was added to a mixture of 0.3 g (3.0 mmol) of piperidin-2-one, the exothermic reaction was stirred for 2 hrs at ambient temperature. Then a solution of 0.38 g (1.5 mmol) of 4′-tert-butyl-2,5-dimethylbiphenyl-4-amine in 5 ml of toluene was added and the reaction mixture was refluxed for 5 hrs. At ambient temperature 5 ml of a 10% aqueous solution of sodium hydroxide was added. Separation of the layers, extraction of the watery layer with 10 ml of toluene, drying over magnesium sulfate, concentration in vacuo and column chromatographic (gradient: cyclohexane->ethyl acetate) yielded 0.3 g (1.0 mmol) 63% of 4′-tert-butyl-2,5-dimethyl-N-[piperidin-2-ylidene]biphenyl-4-amine; log P (pH 2.3)=2.6.
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