반응 #62566

반응 방정식

compound

3-Benzyl-1,5-epoxy-1,2,4,5-tetrahydro-3-benzazepin oxalate

NaOH

→

3-H-epoxybenzazepin

수율 69.4%

용매

methanol

methanol

반응 조건

후처리

1. 1
   기타for 3.5 hours
2. 2
   여과filtered through Celite
3. 3
   기타evaporated
4. 4
   기타The residue was partitioned between H2O and CH2Cl2
5. 5
   건조the organic layer was dried (Na2SO4)

실험 절차

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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