Yield:4950-92-9 84%

Reaction Conditions:

with sodium hydroxide;sodium sulfate in tetrahydrofuran;diethyl ether;hexane;water;

Steps:

162.2 step 2

step 2 4-(heptyloxy)benzylamine To a stirred suspension of lithium aluminum hydride (1.928 g, 52.23 mmol) in THF (150 ml) at room temperature under nitrogen was added a suspension of 4-(heptyloxy)benzamide (6.146 g, 26.117 mmol). After refluxing for 22 h, reaction was cooled in an ice bath and quenched in the following order: water (2.09 ml), 15% NaOH (2.09 ml) and water (6.26 ml). The mixture was stirred for 3 h followed by the addition of Na₂SO₄. The mixture was filtered and concentrated in vac. The residue was taken up in Et₂O, filtered, concentrated, and the resulting residue taken up in hexane, filtered, concentrated, and dried to give the desired product as a hazy yellow oil (4.872 g, 84%): ¹H NMR (400 MHz, DMSO-d₆) δ0.86 (t, J=7 Hz, 3H), 1.22-1.42 (m, 8H), 1.64-1.72 (m, 2H), 1.82 (broad s, 2H), 3.13 (s, 2H), 3.89 (t, J=6.6 Hz, 2H), 6.80-6.84 (m, 2H), 7.17-7.21 (m, 2H); IR (film) 2940, 2850, 1510, 1250 cm^-1; mass spectrum [(+)ESI], m/z 222 (M+H)⁺.

References:

US6214877,2001,B1