Ammonium Chloride → HCID 178442049, compound

Participants

Reaction Steps

The desired product was prepared using a procedure similar to step 6 of example 3. Thus, [4-(1-methyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetonitrile (0.152 g, 0.372 mmol) was reacted with NaN3 (0.121 g, 1.860 mmol) and NH4Cl (0.099 g, 1.860 mmol) in DMF (5 ml) to give the product (0.117 g, 0.259 mmol, 70%) as a white solid, dec. 181-185° C. 1H NMR (DMSO-d6) δ 0.76 (t, J=7.0 Hz, 3H), 1.13-1.22 (m, 4H), 1.51-1.57 (m, 2H), 2.66 (t, J=7.5 Hz, 2H), 3.56 (s, 3H), 5.53 (s, 2H), 7.15 (d, J=8.7 Hz, 2H), 7.42-7.45 (m, 3H), 7.48 (t, J=8.6 Hz, 2H), 7.54 (t, J=7.2 Hz, 2H), 7.65 (d, J=8.7 Hz, 2H), 7.74 (d, J=1.2 Hz, 1H), 16.80 (broad s, 1H); IR (solid) 3030, 2930, 2860, 1605, 1520, 1480, 1370 and 1240 cm−1; [ESI(−)], m/z 450 (M−H)−; Anal. Calcd. for C28H29N5O: C, 74.48; H, 6.47; N, 15.51 Found: C, 74.49; H, 6.26; N, 15.30.

Provenance & Evidence