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Chapter 6
Synthesis of benzodiazepines
Spectral data of the synthesized compounds
2-chloro-N-(2-(4-fluorobenzoyl)phenyl)acetamide ADZ-02. White solid, mp 126-
128 ° C; R f 0.49 (8:2 hexane-EtOAc); IR (KBr): 3373, 3072, 2895, 2828, 1694, 1635,
1482, 1343, 1298 cm -1 ; MS (m/z): 291 [M + ]; Anal. Calcd for C 15 H 11 ClFN 2 O 2 : C,
61.76; H, 3.80; N, 4.80; Found: C, 61.74; H, 3.82; N, 4.82.
5-(4-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one ADZ-03. White solid, mp
172-174 ° C; R f 0.42 (8:2 hexane-EtOAc); IR (KBr): 3182, 3120, 3068, 3051, 2955,
1693, 1672, 1504, 1232, 1024, 839, 810, 731, 690 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ):
δ 4.31 (S, 2H, CH 2 ), 7.04-7.09 (m, 2H, Ar), 7.15-7.19 (m, 2H, Ar), 7.26-7.33 (m, 1H,
Ar), 7.49-7.57 (m, 3H, Ar), 8.83 (s, 1H, NH); MS (m/z): 254 [M + ]; Anal. Calcd for
C 15 H 11 FN 2 O 2 : C, 70.86; H, 4.36; N, 11.02; Found: C, 70.84; H, 4.34; N, 11.03.
5-(4-fluorophenyl)-1-methyl-1H-benzo[e][1,4]diazepin-2(3H)-one ADZ-04a.
White solid, mp 112-114 ° C; R f 0.38 (8:2 hexane-EtOAc); IR (KBr): 3072, 2895, 2828,
1694, 1635, 1482, 1343, 1298, 1050, 880, 834, 756 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ):
δ 3.42 (s, 3H, CH 3 ), 3.75-3.78 (d, 1H, CH, J=10.5Hz), 4.78-4.81 (d, 1H, CH,
J=10.5Hz), 7.05-7.10 (m, 2H, Ar), 7.20-7.29 (m, 1H, Ar), 7.32-7.37 (m, 2H, Ar),
7.54-7.65 (m, 3H, Ar); 13 C NMR: (100 MHz, CDCl 3 ): δ 34.23, 56.53, 114.83, 115.05,
121.33, 123.69, 127.67, 129.62, 131.30, 131.39, 131.45, 134.72, 134.75, 143.54,
162.19, 164.66, 168.13, 169.30; MS (m/z): 268 [M + ]; Anal. Calcd for C 16 H 13 FN 2 O: C,
71.63; H, 4.88; N, 10.44; Found: C, 71.64; H, 4.84; N, 10.42.
1-ethyl-5-(4-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one ADZ-04b. Yellow
solid, mp 162-164 ° C; R f 0.44 (8:2 hexane-EtOAc); IR (KBr): 3078, 2865, 2821, 1686,
1620, 1462, 1341, 1298, 1054, 834, 780 cm -1 ; MS (m/z): 282 [M + ]; Anal. Calcd for
C 17 H 15 FN 2 O: C, 72.32; H, 5.36; N, 9.92; Found: C, 72.34; H, 5.38; N, 9.96.
5-(4-fluorophenyl)-1-propyl-1H-benzo[e][1,4]diazepin-2(3H)-one ADZ-04c.
Yellow solid, mp 123-125 ° C; R f 0.30 (8:2 hexane-EtOAc); IR (KBr): 3068, 3024,
2958, 2900, 1684, 1495, 1482, 808, 732, 690 cm -1 ; MS (m/z): 296 [M + ]; Anal. Calcd
for C 18 H 17 FN 2 O: C, 72.95; H, 5.78; N, 9.45; Found: C, 72.95; H, 5.78; N, 9.46.
Department of Chemistry, Saurashtra University, Rajkot-360005 218