Methanol → 7-morpholino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-3-amine

Participants

Reaction Steps

Into a Parr pressure reactor was added 4-(2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-morpholine (200 mg, 0.0007 mol) in methanol (6 mL, 0.1 mol). The reaction was placed under 40 psi for 10 h. HPLC indicated no starting material remaining. The reaction mixture was filtered through celite. The celite was further washed with methanol and DMF. The filtrated was concentrated in vacuo to a tannish-brown solid which was confirmed as product by both 1HNMR and LCMS. Material was carried on without further purification to give 7-Morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine. 1HNMR (400 MHz, CDCl3) δ 6.89 (d, 1H, J=7.8 Hz), 6.49 (s, 1H), 6.45 (d, 1H, J=7.8 Hz), 3.70 (broad s, 4H), 3.52 (broad s, 1H), 2.68-2.77 (m, 2H), 2.56 (broad s, 4H), 2.05 (m, 2H), 1.59 (broad s, 2H), 1.39 (m, 2H), 1.22 (m, 2H).

Provenance & Evidence