2-(2-Bromophenyl)ethan-1-ol → 1-(4-Methoxyphenyl)-4-[2-(5-bromoisochroman-1-yl)ethyl]piperazine

Participants

Reaction Steps

Following the general procedure of EXAMPLE 45 (step 1) and making non-critical variations 2-(o-bromophenyl)-1-ethanol (XLIX, 3.3 g) is converted to ethyl 2-(5-bromoisochroman-1-yl)acetate (LXXI). Following the general procedure of EXAMPLE 45 (Step 2) and making non-critical variations ethyl 2-(5-bromoisochroman-1-yl)acetate (LXXI, 1.0 g) is hydrolyzed to the corresponding acid, 2-(5-bromoisochroman-1-yl)acetic acid (LXXII). This acid (LXXII, 740 mg) is coupled with p-methoxyphenylpiperazine (V) and the resulting amide, 1-(4-methoxyphenyl)-4-[2-(5-bromoisochroman-1-yl)]acetyl piperazine (LXXIII, 1.10 g) is reduced according to the general procedure described in EXAMPLE 50 (making non-critical variations) to give the title compound, mp 105°-106°.

Provenance & Evidence