Synthesis of 1,5-Benzodiazepine Under Solvent-Free Condition
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N55C–CH–CH2CH3), 1.6–1.4 (m, 8H, CH2–CH2), 1.25–0.85(m, 18H,
CH2–CH2–CH3). C20H32N2 (300.49) Calcd.: C, 79.94; H, 10.73; N, 9.32.
Found: C, 79.75; H, 10.65; N, 9.40. MS: m/z Mþ ¼ 300.
3-Ethyl-2,4-dimethyl-2-n-propyl–2,3-dihydro-1H-1,5-benzodiazepine
(e). Yellow solid. M.p.: 1438C (from ethanol/hexane). UV-Visible (lmax
,
nm): 458, 305, 255. FTIR spectrum (KBr, cm21): 3360 (N-Hstr), 2980
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(alkyl C-Hstr), 1630 (C55Nstr), 1525 (aromatic C55C). HNMR spectrum
(CDCl3, 400 MHz): 7–7.25 (m, 4H, Ar-H), 3.9 (br, s, 1H, N-H), 2.4 (t, 1H,
N55C–CH–CH2CH3), 2.2 (S, 3H, N-C-CH3) 1.85 (s, 3H, N55C–CH3),
1.50–1.75 (m, 2H, CH2CH3), 1.3–0.8 (m, 10H, CH2–CH2CH3). C16H24N2
(244.38) Calcd.: C, 78.64; H, 9.90; N, 11.46. Found: C, 78.55; H, 9.75; N,
11.55. MS: m/z Mþ ¼ 244.
Spirocyclohexan-2,3,4,10,11,11a-hexahydro-1H-dibenzo[b,e][1,4]dia-
zepine (f). Yellow solid. M.p.: 1378C (from ethanol/hexane). UV-Visible
(lmax, nm): 458, 304, 275, 261. FTIR spectrum (KBr, cm21): 3350
(N-Hstr), 2980 (alkyl C-Hstr), 1625 (C55Nstr), 1520 (aromatic C55C).
1HNMR spectrum (CDCl3, 400 MHz): 7–7.3 (m, 4H, Ar-H), 3.8 (br, s, 1H,
N-H), 2.85–3.15 (m, 3H, N55C–CH and N55C–CH2), 1.96–2.75
(m, 8 ꢂ CH2, 16H). C18H24N2 (268.41) Calcd.: C, 80.55; H, 9.01; N, 10.44.
Found: C, 80.45; H, 8.95; N, 10.35. MS: m/z Mþ ¼ 268.
Spirocycloheptan-6,7,8,9,10,10a,11,12-octahydrobenzo[b]cyclo hepta
[e][1,4]diazepine (g). Dark yellow solid. M.p.: 1358C (from ethanol/
hexane). UV-Visible (lmax, nm): 489, 440, 299, 260. FTIR spectrum
(KBr, cm21): 3350 (N-Hstr), 2980 (alkyl C-Hstr), 1625 (C55Nstr), 1520
(aromatic C55C). 1HNMR spectrum (CDCl3, 400 MHz): 7–7.3 (m, 4H,
Ar-H), 3.8 (br, s, 1H, N-H), 2.9–3.2 (m, 3H, N55C–CH and N55C–
CH2), 1.5–2.75 (m, 10 ꢂ CH2, 20H). C20H28N2 (296.46) Calcd.: C,
81.03; H, 9.52; N, 9.45. Found: C, 81.25; H, 9.45; N, 9.40. MS: m/z
Mþ ¼ 296.
2-Methyl-2,4-diphenyl-2,3-dihydro-1H-1,5-benzodiazepine (h). Dark
yellow solid. M.p.: 150–1528C (from ethanol). UV-Visible (lmax, nm): 485,
300, 265. FTIR spectrum (KBr, cm21): 3325 (N-Hstr), 3010 (aromatic C-H
1
str), 2975 (alkyl C-Hstr), 1630 (C55Nstr), 1535(aromatic C55C). HNMR
spectrum (CDCl3, 400 MHz): 6.8-7.55 (m, 14H, Ar-H), 4.1 (br, s, 1H, N-H),
3.1 (s, 2H, N55C-CH2), 1.75 (s, 3H, CH3). C22H20N2 (312.42) Calcd.: C,
84.58; H, 6.45; N, 8.97. Found: C, 84.45; H, 6.53; N, 8.75. MS: m/z
Mþ ¼ 312.
2-Methyl-2,4-di(4-chlorophenyl)-2,3-dihydro-1H-1,5-benzodiazepine
(i). Dark yellow solid. M.p.: 160–1638C (from ethanol). UV-Visible (lmax
,
nm): 475, 310, 260. FTIR spectrum (KBr, cm21): 3330 (N-Hstr), 3010
(aromatic C-Hstr), 2950 (alkyl C-H str), 1625 (C55Nstr), 1520 (aromatic
1
C55C). HNMR spectrum (CDCl3, 400 MHz): 6.85–7.45 (m, 12H, Ar-H),