Amosulalol


Amosulalol is an antihypertensive drug. It has much higher affinity for α1-adrenergic receptors than for β-adrenergic receptors. It is not approved for use in the United States.

Synthesis

Guaiacol reacts with ethylene oxide to give 2-ethanol. Halogenation with thionyl chloride converts the alcohol group to a chloride,, which is used to alkylate benzylamine to give the secondary amine. This forms a tertiary amine when combined with 5-bromoacetyl-2-methylbenzenesulfonamide. The reduction of the carbonyl group with sodium borohydride produces and catalytic hydrogenation removes the benzyl group, yielding amosulalol.