Sodium Hydroxide → 3-H-epoxybenzazepin

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Reaction Steps

A solution of the compound prepared in Example 18 (6.1 g, 0.018M) in methanol (300 ml) was hydrogenated (0.61 g, 10% Pd-C) in a Parr apparatus at an initial pressure of 30 psi for 3.5 hours. The resulting solution of the product in methanol was made basic with aqueous NaOH, filtered through Celite and evaporated. The residue was partitioned between H2O and CH2Cl2 ; the organic layer was dried (Na2SO4) to give 3-H-epoxybenzazepin (1.95 g, 68% yield). This compound was treated with acetic anhydride (6 ml) and allowed to stir for two hours. Excess acetic anhydride was removed in vacuo to give 3-acetylepoxybenzazepin as a white solid (2.2 g), mp 126°-128° C. NMR (CDCl3) δ 1.80 ppm (s, 3H, --CH3), 3.10-4.45 (m, 4H, --CH2 --N--CH2), 5.20 [m, 2H, (2x), ArCHO], 7.30 (s, 4H, aromatic H). MS: 203 (M+).

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