Tert-Butylamine → Spirendolol

Participants

Reaction Steps

7.5 g of a mixture of mainly 4'-(3-chloro-2-hydroxypropoxy)-spiro(cyclohexane-1,2'-indan)-1'-one and of 4'-(2,3-epoxypropoxy)-spiro(cyclohexane-1,2'-indan)-1'-one in 50 ml dioxane and 30 ml tert.-butylamine are heated at 130° for 20 hours in an autoclave, then cooled and partitioned between 2 N tartaric acid and ether. The aqueous phase is made alkaline and extracted with ether. The organic phases are evaporated to yield the title compound in free base form (M.Pt. 87°-88°) which is converted into the hydrogen maleate; M.Pt. 180°-181°, and hydrogen malonate M.Pt. 143°-145°.

Provenance & Evidence