Phenethylamine → HCID 4220578, compound

Participants

Reaction Steps

A suspension of 31.4 mL of phenethylamine (0.25 mol) and 42.6 g of DL-mandelic acid (0.28 mol, 1.12 eq.) in 600 mL of xylenes was heated to reflux with a Dean-Stark water separator for 8 hr. The reaction was cooled, and the xylenes removed in vacuo. The resulting residue was partitioned between saturated NaHCO3 and CH2Cl2. The CH2Cl12 layer was dried (Na2SO4) and the solvents removed to yield a solid which was recrystallized from THF to yield, after drying, 56 g of hydroxyamide (88%) as a white, crystalline solid, mp 95°-96° (Lit 97°-98° ) To 350 g of PPA at 25° was added 30.7g of this solid (120 mmol) with mechanical stirring. The reaction was heated to 65° for 2 hr, then poured onto ice in a 4L beaker. The resulting suspension was stirred vigorously, the solids pulverized under H2O and filtered, washing well with H2O. Drying of the solid in vacuo and recrystallization from absolute EtOH provided 27 g of 1-phenyl-1,3,4,5-tetrahydro-3(2H)-benzazepin-2-one (95%) as a white solid, mp 189°-191° .

Provenance & Evidence