Formaldehyde → HCID 18965718, compound

Participants

Reaction Steps

Reductive methylation of N[3(Diethylamino)propyl]-2-hydroxy-3-methyl-5-iodo-benzylamine dihydrochloride (5 mmol, from last step) formaldehyde (5 mL, 37% solution) and sodium cyanoborohydride (0.63 g, 10 mmol) in methanol (25 mL), work-up, conversion to the dihydrochloride (conc. hydrochloric acid, 5 mL), evaporation to dryness in vacuo and crystallization of the resulting material from methanol-acetone as described for Example 1 gave the title compound as colorless crystals. Yield(overall): 1,945 g (84%); mp. 166°-168° C. NMR (CDCl3, free base): δ0.97 (t, 6H, J-6 Hz, --CH2 --CH3); 1.5-1.9 (m, 2H, --CH2 --); 2.13 (s, 3H, --CH3); 2.23 (s, 3H, --CH3); 2.3-2.7 (m, 8H, N--CH2); 3.6 (s, 2H benzylic CH2), 7.1 (d, 1H, J=1 Hz, aromatic H); 7.35 (d, 1H, J=1 Hz, aromatic H); IR (KBr): 3420, 2940, 2640, 1625, 1470, 1390, 1210 cm-1. Analysis found: C, 41.47; H, 6.24; N, 5.93. C16H29Cl2IN2O requires: C, 41.49; H, 6.31; N, 6.05.

Provenance & Evidence