Methoxyacetic Acid → 1-[1-(Diphenylmethyl)azetidin-3-yl]-4-(methoxyacetyl)-piperazine

Participants

Reaction Steps

To a solution of 1-[1-(diphenylmethyl)azetidin-3-yl]piperazine (see Method 7a; 615 mg, 2.0 mmol) in DMF (8 mL) were added methoxy acetic acid (272 mg, 3.0 mmol), DIPEA (310 mg, 2.4 mmol) and TBTU (770 mg, 2.4 mmol). The reaction mixture was stirred at RT for 12 h and then partitioned between methylene chloride and aqueous NaHCO3. The aqueous phase was extracted twice with methylene chloride and then the combined organic solutions were washed with brine and dried over MgSO4. The solvent was removed by evaporation and the product was purified by means of reversed phase chromatography is using a mixture of acetonitrile and aqueous 0.1 M ammonium acetate as eluent. There was obtained 610 mg (80%) of 1-[1-(diphenylmethyl)azetidin-3-yl]-4-(methoxyacetyl)-piperazine. 1H NMR (500 MHz, CD3OD): 2.3-2.4 (m, 4H), 3.0 (m, 3H), 3.4 (s, 3H), 3.4 m, 2H), 3.5 (m, 2H), 3.6 (m, 2H), 4.1 (s, 2H), 4.5 (s, 1H), 7.2 (t, 2H), 7.3 (t, 4H), 7.4 (d, 41-1); LCMS: m/z 380 (M+1)+.

Provenance & Evidence