Diethyl Ether → 2,3-Dihydro-1,3-dibutyl-2-octyl perimidine

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Reaction Steps

A mixture of N,N'-dibutyl-1,8-naphthalene diamine (prepared in Example 2) (1.35 g, 5 mmol), nonyl aldehyde (0.78 g, 5.5 mmol), p-toluene sulfonic acid (5 mg) and ethyl acetate (5 ml) was prepared and stirred at room temperature for 15 minutes. More nonyl aldehyde (0.16 g, 1.1 mmol) was added to complete the reaction. The mixture was diluted with ether (50 ml), washed with saturated sodium carbonate (10 ml), washed with water and brine, and dried over potassium carbonate. The extract was concentrated to an oil that would not crystallize from ethyl acetate-hexane. The oil was dried under vacuumn to give crude 2,3-dihydro-1,3-dibutyl-2-octyl perimidine: NMR (CDCl3) 7.05(m, 4H), 6.35(d, 2H), 4.10(t, 1H), 3.5 and 3.0(m, 4H), 1.8-1.0(m, 20H), 0.9(t, 9H).

Provenance & Evidence