2-CHLORO-1-(10,11-DIHYDRO-DIBENZO[B,F]AZEPIN-5-YL)-ETHANONE synthesis

Yield:3534-05-2 95%

Reaction Conditions:

in toluene at 90; for 4 h;Inert atmosphere;

Steps:

16 2-Chloro-1-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)ethan-1-one( 15)

General procedure: 4.1.1.16
2-Chloro-1-(7-chlorodibenzo[b,e] [1,4]oxazepin-5(11H)-yl)ethan-1-one (14)
In a typical procedure, to a solution of 6 (0.59 g, 3 mmol) in toluene (30 mL), chloroacetyl chloride (0.34 g, 3 mmol) was added.
The mixture was stirred at reflux for 4 h.
After that, the solvent was evaporated in vacuo.
Purification of the residue by chromatography (CH₂Cl₂) afforded 14 as white crystals (0.54 g, 58%). 2-Chloro-1-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)ethan-1-one( 15). The title compound wasprepared from iminodibenzyl (0.98 g, 5 mmol)and chloroacetyl chloride (0.56 g, 5 mmol) in toluene (50 mL) in a similarmanner as described for 14. Purification of the residue by chromatography (CH₂Cl₂)afforded 15as white needles (1.29 g, 95%). mp 98-99 °C; FTIR 1685 cm^-1;¹HNMR (400 MHz, Chloroform-d) δ 7.41 - 7.00 (m, 8H), 3.96 (d, J =22.8 Hz, 2H), 3.49 - 3.22 (m, 2H), 2.87 - 2.69 (m, 2H); ¹³C NMR (101MHz, cdcl₃) δ 166.29, 141.08, 139.68, 138.07, 134.62, 130.89,130.40, 129.37, 128.34, 128.05, 127.72, 127.25, 126.88, 41.87, 30.93, 30.42; MS (APCI) calcd for C₁₆H₁₄ClNO:271.08: found 272.0844; purity (HPLC): 100%.

References:

Marcu, Ana;Schurigt, Uta;Müller, Klaus;Moll, Heidrun;Krauth-Siegel, R. Luise;Prinz, Helge [European Journal of Medicinal Chemistry,2016,vol. 108,p. 436 - 443] Location in patent:supporting information