Methane → HCID 19820515, compound

Participants

Reaction Conditions

Reaction Steps

A flask containing 2-methylthio-1,4,5,6,7,8-hexahydro-1,3-diazocine hydroiodide (3.00 g, 1.05×10-2 mole) and 2,2-diphenylethylamine (2.08 g, 1.05×10-2 mole) was immersed in an oil bath which had been preheated to ca. 155° C. The reaction was stirred at between 150°-160° C. for ca. 1 hour. The resulting yellow glass was dissolved in methanol. The methanol was evaporated leaving a foam which was dissolved in a two phase mixture of 5 molar aqueous NaOH (65 ml) and CH2Cl2 (60 ml). After stirring overnight the CH2Cl2 layer was separated. The aqueous alkaline layer was extracted with CH2Cl2 (2×). The CH2Cl2 layers were combined, washed with H2O (2×), washed with saturated aqueous NaCl, and dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure leaving a foam. The foam was dissolved in methanol (15 ml) and the solution was cooled to 0° C. This solution was then treated with a methanolic solution of HCl. The solution was treated with charcoal which was subsequently removed by filtration through a pad of celite. The filtrate was concentrated on the steam bath and 2-butanone was added periodically until the temperature of the solution reached ca. 80° C. Upon cooling the solution deposited a solid which was collected by filtration. This material was recrystallized two times from methanol/2-butanone affording 2-(2,2-diphenylethylamino)-1,4,5,6,7,8-hexahydro-1,3-diazocine hydrochloride as an off-white solid: 0.80 g (22%), m.p. 195°-197° C.

Provenance & Evidence