Dimethylamine → 5-(3-Dimethylamino-2-hydroxypropyl)-5-hydroxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

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Reaction Steps

A mixture of 3.7 g (14 mmol) of the epoxide 11, 26.8 g (0.59 mol) of anhydrous dimethylamine, and 50 ml of EtOH was heated at 100° C. in a stainless steel autoclave for 12 hrs. When cool the contents were removed and concentrated under reduced pressure. Recrystallization of the solid residue from aqueous EtOH afforded 1.6 g (37% yield) of the crystalline amino-diol 12, m.p. 144°-146° C.

Provenance & Evidence