Alkoxybenzhydrylalkylamines and their acid addition salts

Abstract

The title amines (I) are prepd. by reaction of the corresponding alkoxybenzylidenealkylamine (II) with PhLi followed by hydrolysis. Thus, 32 g. PhBr was added dropwise to 2.8 g. Li wire in 100 ml. dry Et2O under N. To the product was added 11.3 g. 4-methoxybenzylidenepropylamine in 30 ml. Et2O and the mixt. shaken for 2 hrs. to give 82.6% I (R = 4-MeO, R1 = Pr), b12 199-202 Deg; hydrochloride m. 164-5 Deg (MeOH-Et2O). Similarly prepd. were the following I (R, R1, m.p. HCl, and % yield given): 2-MeO, Pr, 193-5 Deg, 61; 2-EtO, Me, 207-10 Deg, 52; 2-EtO, Pr, 195-7 Deg, 51.3; 2-PrO, Me, 157-8 Deg, 76; 2-BuO, Me, 153-4 Deg, 72; 2-BuO, Pr, 123-5 Deg, 77; 3-MeO, Me, 223 Deg, 72.3; 3-MeO, Pr, 193 Deg, 75.6; 3-EtO, Me, 232 Deg, 72.3; 3-EtO, Pr, 200 Deg, 80.7; 3-PrO, Me, 153 Deg, 78; 3-PrO, Pr, 175 Deg, 80.2; 3-PrO, Bu, 160 Deg 74.1; 3-BuO, Me, 94-5 Deg, 74; 3-BuO, Pr, 170-2 Deg, 77.1; 3-EtO, Et, 165 Deg, 78.4; 3-EtO, Bu, 176-7 Deg, 80.6; 3-BuO, Et, 108 Deg, 75.6; 3-BuO, Bu, 152 Deg, 77.9; 4-MeO, Me, 175 Deg, 81.2; 4-MeO, Et, 104-5 Deg, 81. I exhibit anesthetic properties.