Methanol → Isopropylamine

Participants

Reaction Steps

In a similar manner to the preparation of 18, compound 23 was obtained from 4′-(2,3-epoxy-propoxy)-4-methoxy-chalcone, 13 (1 g, 3.2 mmol) and iso-propyl amine (1.36 mL, 16 mmol) in dry methanol (100 mL). Yield 700 mg (59%); mp 105-106° C.; MS (FAB) 370 (M++1); IR (KBr) 3420, 3289, 1654; 1H NMR (200 MHz, CDCl3) δ 8.02 (d, J=8.6 Hz, 2H), 7.78 (d, J=15.7 Hz, 1H), 7.60 (d, J=8.5 Hz, 2H), 7.42 (d, J=15.6 Hz, 1H), 6.99 (d, J=8.9 Hz, 2H), 6.93 (d, J=8.7 Hz, 2H), 4.23-4.09 (m, 3H), 3.85 (s, 3H), 2.96-2.74 (m, 3H), 1.11 (d, J=6.2 Hz, 6H). Analyses calculated for C22H27NO4: C, 71.52; H, 7.37; N, 3.79. Found: C, 71.33; H, 7.42; N, 3.63.

Provenance & Evidence