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Chapter 6
Synthesis of benzodiazepines
5-(4-fluorophenyl)-1-isopropyl-1H-benzo[e][1,4]diazepin-2(3H)-one ADZ-04d.
White solid, mp 98-100 ° C; R f 0.25 (8:2 hexane-EtOAc); IR (KBr): 3118, 3067, 3054,
2958, 2901, 1683, 1582, 1469, 810, 705 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 1.22-
1.24 (d, 3H, CH 3 ), 1.50-1.60 (d, 3H, CH 3 ), 3.70-3.74 (d, 1H, CH), 4.53-4.58 (m, 1H,
CH), 4.68-4.71 (d, 1H, CH), 7.05-7.11 (m, 2H, Ar), 7.23-7.26 (m, 1H, Ar), 7.42-7.52
(m, 3H, Ar), 7.61-7.63 (m, 2H, Ar); 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, 72.97; H, 5.79; N, 9.47.
1-butyl-5-(4-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one ADZ-04e. Yellow
solid, mp 88-90 ° C; R f 0.28 (8:2 hexane-EtOAc); IR (KBr): 3154, 3085, 2968, 2910,
1685, 1564, 1420, 1350, 1232, 854, 696 cm -1 ; MS (m/z): 310 [M + ]; Anal. Calcd for
C 19 H 19 FN 2 O: C, 73.53; H, 6.17; N, 9.03; Found: C, 73.57; H, 6.19; N, 9.07.
5-(4-fluorophenyl)-1-isobutyl-1H-benzo[e][1,4]diazepin-2(3H)-one ADZ-04f.
Yellow solid, mp 72-74 ° C; R f 0.34 (8:2 hexane-EtOAc); IR (KBr): 3156, 3058, 2968,
2905, 1985, 1564, 1369, 810, 694 cm -1 ; MS (m/z): 310 [M + ]; Anal. Calcd for
C 19 H 19 FN 2 O: C, 73.53; H, 6.17; N, 9.03; Found: C, 73.50; H, 6.11; N, 9.10.
5-(4-fluorophenyl)-1-pentyl-1H-benzo[e][1,4]diazepin-2(3H)-one ADZ-04g. White
solid, mp 93-95 ° C; R f 0.25 (9:1 Chloroform: Methanol); IR (KBr): 3110, 3056, 2956,
2845, 1345, 1254, 1056, 842, 730, 698 cm -1 ; MS (m/z): 324 [M + ]; Anal. Calcd for
C 20 H 21 FN 2 O: C, 74.05; H, 6.53; N, 8.64; Found: C, 74.07; H, 6.59; N, 8.67.
5-(4-fluorophenyl)-1-isopentyl-1H-benzo[e][1,4]diazepin-2(3H)-one ADZ-04h.
Yellow solid, mp 84-86 ° C; R f 0.23 (8:2 hexane-EtOAc); IR (KBr): 3125, 3089, 3021,
2985, 1236, 1056, 854, 795, 830, 698 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): δ 0.64-0.71
(dd, 6H, 2 x CH 3 ), 1.22-1.33 (m, 1H, CH), 3.51-3.57 (m, 1H, CH), 3.63-3.66 (d, 1H,
CH), 4.28-4.35 (m, 1H, CH), 4.62-4.65 (d, 1H, CH), 5.19 (s, 2H, CH 2 ), 6.95-7.00 (m.
2H, Ar), 7.10-7.14 (m, 1H, Ar), 7.17-7.19 (m, 1H, Ar), 7.32-7.34 (d, 1H, J=8.28Hz
Ar), 7.45-7.53 (m, 3H, Ar); 13 C NMR: (100 MHz, CDCl 3 ): δ 22.10, 22.54, 25.48,
36.65, 44.74, 53.52, 57.14, 115.16, 115.37, 122.17, 124.33, 129.92, 130.13, 131.33,
131.42, 131.48, 134.94, 134.97, 142.63, 162.89, 165.38, 168.93, 169.36; MS (m/z):
324 [M + ]; Anal. Calcd for C 20 H 21 FN 2 O: C, 74.05; H, 6.53; N, 8.64; Found: C, 74.10;
H, 6.65; N, 8.77.
Department of Chemistry, Saurashtra University, Rajkot-360005 219