1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-((tetrahydro-2H-pyran-4-yl)methyl)-2-(4-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)phenoxy)acetamide

Participants

Reaction Steps

To a solution of the product of step 4 (23 g, 0.0602 moles) in DMF (69 mL), (tetrahydro-2H-pyran-4-yl)methanamine (7.6 gm, 0.0662 moles), HOBT (50 mg, catalytic amount), EDC.HCl (17.5 g, 0.0903 moles) and DMAP (50 mg, catalytic amount) were added and reaction mixture was srirred at 25° C. for 16 hours. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evapourated under reduced pressure. The crude product was purified by coloumn chromatography using ethyl acetate:Hhexane (1:1) as eluent to yield 16.5 g (57%) of product as white solid. 1H NMR: DMSO-d6 δ 1.10 (t, J=6.6 Hz, 3H), 1.13-1.16 (m, 2H), 1.46-1.49 (m, 2H), 1.61-1.70 (m, 1H), 2.74 (q, J=7.6 Hz, 2H), 3.01 (t, J=6.6 Hz, 2H), 3.17-3.23 (m, 2H), 3.78-3.81 (dd, J=11.4 & 2.6 Hz, 2H), 4.51 (s, 2H), 5.26 (s, 2H), 6.96 (dd, J=6.8 & 2.0 Hz, 2H), 5.57-5.61 (m, 4H), 7.72 (d, J=8.0 Hz, 2H), 8.10 (t, J=6.0 Hz, NH).

Provenance & Evidence