Methylamine → HCID 9817507, compound

Participants

Reaction Steps

A solution of 6.2 g of 2-(2-chloroethoxy)-1-[2-(chloromethyl)phenoxy]benzene in 310 ml ethanol was added at room temperature in 45 min to a solution of 80 ml of methylamine in 1.2 1 of abs. ethanol. The mixture was stirred overnight, concentrated and dissolved in 100 ml of dimethyl sulphoxide. 18.6 ml of triethylamine were added and the reaction mixture was heated to 90°-100° C. and stirred overnight. After cooling the mixture was poured into 4.5 1 of ice water and extracted with 3×600 ml of dichloromethane. The extract was washed with water, dried over sodium sulphate and concentrated in vacuo. The crude product obtained was purified by silica chromatography with dichloromethane-acetone (9:1), after which the free base was converted into the hydrochloric salt, to obtain 2.12 g (35%) of 6,7,8,9-tetrahydro-8-methyl-dibenzo[b,i][1,4,7]dioxazecine hydrochloride. Mp 223° C.

Provenance & Evidence