Acetic Acid → 3-Acetyl-1-(1,3-dioxolan-2-yl)-1,5-epoxy-1,2,4,5-tetrahydro-3-benzazepin

Participants

Reaction Steps

A suspension of 10% Pd-C (1.42 g) in a solution of the product from Example 29 (9.75 g, 0.0302M) and glacial acetic acid (12 ml) in absolute ethanol (130 ml) was hydrogenated in a Parr apparatus at an initial pressure of 32 psi. After six hours, the catalyst was removed by filtration through Celite and the solvents. removed in vacuo. The residue was taken up in CH2Cl2 (50 ml) and treated with acetic anhydride (6.0 ml). After 15 minutes, the mixture was evaporated to dryness and the residue crystallized from Et2O to give the titled compound (7.34 g, 88% yield) as white crystals, mp 122°-123° C. NMR (CDCl3) δ 1.73 ppm (s, 3H, COCH3), 3.0-4.60 (m, 8H, ##STR49## and --OCH2CH2O--), 5.17 (m, 2H, ##STR50## 7.25 (m, 4H, aromatic H). IR (KBr): 1653 cm-1 (C=O). MS: 275 (M+).

Provenance & Evidence