Methylamine → 4-(2-(4-Hydroxycyclohexyl)-1-(4-(2-(methylamino)ethoxy)-phenyl)but-1-enyl)phenol

Participants

Reaction Steps

Following the same procedure as described in example 11, step D, 4-(1-(4-(2-chloroethoxy)phenyl)-2-(4-hydroxycyclohexyl)but-1-enyl)phenol (0.8 g, 1.0 eq) was reacted with MeNH2 (30% wt in water, 10 mL) in MeOH (20 mL) at reflux to give 20 mg desired product (3% yield, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.03 (d, J=8.4 Hz, 2H), 6.94 (d, J=8.4 Hz, 2H), 6.78 (d, J=8.4 Hz, 2H), 6.71 (d, J=8.4 Hz, 2H), 4.04 (t, J=4.8 Hz, 2H), 2.96 (t, J=4.8 Hz, 2H), 2.50 (s, 3H), 2.36-2.47 (m, 1H), 2.04 (q, J=7.6 Hz, 2H), 1.90-2.01 (m, 2H), 1.40-1.80 (m, 6H), 0.87 (t, J=7.6 Hz, 3H); m/z=396[M+1]+.

Provenance & Evidence