Synthesis and ring-expansion of 4-(2-dimethylaminoethyl)-4-methylnaphthalen-1(4H)-one and its 2,3-dihydro-derivative and some reactions of the lactam products

Abstract

The title compounds, (3) and (6), were prepared by subjecting the methiodides of 3,4,5,6-tetrahydro-3,6-dimethyl-2,6-methano-3-benzazocin-1(2H)-one (2) and 1-α-hydroxy-1,2,3,4,5,6-hexahydro-3,6-dimethyl-2,6-methano-3-benzazocine (7) to a Hofmann elimination reaction. Beckmann rearrangements of the oximes of compounds (3) and (6) gave the acylanilide-type lactam products, (13) and (8), respectively. A Schmidt ring expansion of the 4,4-disubstituted 1-tetralone (6) also gave (8) whilst a similar reaction on the 4,4-disubstituted 1-tetralone (3) gave a primary amine, probably (4). The lactam (8) was reduced to (9) and alkylated, to give (10).