Abstract
As new derivatives of phenylmorpholine having epinephrine-like activity, 2-(3, 4-dihydroxyphenyl)-N-methylmorpholine and 2-(3, 4-dimethoxyphenyl)-N-methylmorpholine were prepared. Isoquinoline-type cyclization of 2-(3, 4-dialkoxyphenyl) morpholine hydrochloride with formaldehyde afforded a new type 1H-2, 5-benzoxazine ring. Debenzylation of its dibenzyloxy compound by catalytic reduction over palladium-charcoal afforded 3, 4, 5, 6-tetrahydro-8, 9-dihydroxy-1, 5-methano-1H-2, 5-benzoxazine. Pharmacological tests revealed that some of these new derivatives possessed antitussive action better than that of codeine and 2-(3, 4-diacetoxyphenyl)-N-methylmorpholine seemed to be the most desirable of such compounds.
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