Quinone → HCID 10007683, compound

Participants

Reaction Steps

To a solution of p-benzoquinone (0.1 g; 0.92 mmol) in 70 ml of MeOH was added when cold N1-ethyl-N1-(2-methoxy-benzyl)-propan-1,3-diamine (0.45 g; 2.0 mmol). The reaction mixture was agitated at e.t. and out of the light for 6 h, the was evaporated in a vacuum to give a crude material which was purified by flash chromatography. Eluting with CH2Cl2/MeOH/NH4OH 9.75:0.25:0.025 obtained 0.23 g of the compound XII as a pure red solid on TLC (eluant: CHCl3/MeOH/NH4OH 9.5:0.5:0.05). Yield 45%; 1H NMR (free base; CDCl3) δ: 1.11 (t, 6H), 1.72-1.85 (m, 4H), 2.56 (q, 8H), 3.18 (q, 4H), 3.62 (s, 4H), 3.82 (s, 6H), 5.26 (s, 2H), 6.83-6.95 (m, 4H), 7.19-7.43 (m, 4H+2H exchangeable with D2O); EI-MS: m/z=548 (M+).

Provenance & Evidence