Ammonia → (4-{4-[3-(2,5-Dimethylpyrrolidin-1-yl)propoxy]phenyl}tetra-hydro-pyran-4-ylmethyl)dimethylamine

Participants

Reaction Steps

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (330 mg, 1.43 mmol), 1-(3-chloro-propyl)-2,5-trans-dimethyl-pyrrolidine (221 mg, 1.26 mmol), DMF (7.6 ml) and K2CO3 (790 mg, 5.72 mmol) were reacted together according to general procedure B. The isolated material was subjected to chromatography on silica, eluant 95:4:1 (DCM, MeOH, NH3) to give the title compound as a yellow oil (180 mg, 34%). 1H NMR (400 MHz, CDCl3) δ7.20 (d, 2H), 6.87 (d, 2H), 4.08-3.95 (m, 2H), 3.79-3.70 (m, 2H), 3.59-3.49 (m, 2H), 3.11-3.00 (m, 2H), 2.77 (m, 1H), 2.54 (m, 1H), 2.40 (s, 2H), 2.14-1.81 (m, 8H), 1.96 (s, 6H), 1.44-1.31 (m, 2H), 0.97 (d, 6H).

Provenance & Evidence