Morpholine → HCID 23469680, compound

Participants

Reaction Steps

A mixture of 4-hydroxy-α-isopropylbenzyl alcohol (1.0 g; 0.006 mol) morpholine (1.3 g; 0.015 mol) and water (1.3 ml) is refluxed under a nitrogen atmosphere for 23 hours, and then poured into water (~20 ml). The aqueous solution is extracted with 30 ml of ether, the ethereal solution dried over magnesium sulfate, and concentrated to give 0.97 g of crude product (69% of theory). Recrystallization of the crude product from methylene chloride affords pure title compound (490 mg 35%): mp 142°-143° C.; IR (Nujol) 3300 (s), 2940 (s), 1610 (m), 1595 (m) cm-1 ; NMR (CDCl3) δ0.75 and 0.92 (a pair of d, J=7 Hz, 6 H, two methyls), 1.8-2.4 (m, 1 H, isopropyl methine proton), 2.3-2.5 (m, 4 H, two methylene groups adjacent to the nitrogen atom), 2.94 (d, J=8 Hz, 1 H, benzylic proton), 3.6-3.9 (m, 4 H, two methylene groups adjacent to the oxygen atom), 3.9-6.2 (broad s, 1 H, phenoxy proton) and 6.75 and 7.05 ppm (AB quartet, J=8 Hz, 4 H, aromatic). Anal. Calcd for C14H21NO2 : C, 71.45; H, 8.95; N, 5.95. Found: C, 71.07; H, 8.64; N, 6.01.

Provenance & Evidence