Med Chem Res (2011) 20:975–980
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Table 2 Spectral data of synthesized compounds 5a–e
Compd. IR (kmax/cm-1
)
1HNMR (d/ppm)
13CNMR (d/ppm)
5a
5b
5c
5d
3350, 3025, 2918,
1730, 1682, 1370,
1155
1.09 (q, 2H), 1.37 (t, 2H), 1.86 (s, 6H), 2.15 (s, 3H), 17.5 (CH3), 19.3, 24.9, 49.7 (CH2–CH2–CH2–), 22.6
(CH3), 47.5, 53.8 (N–CH2–CH2–N), 68.5 (CH),
120–125 (Ar–C), 169.7 (CONH), 193.7 (C=O)
2.35 (t, 2H), 2.42–2.75 (complicate, 8H) 4.12 (m,
1H), 7.62–7.85 (m, 4H), 10. 38 (s, 1H)
3345, 3017, 2915,
1735, 1680, 1370,
1145
1.10 (q, 2H), 1.42 (t, 2H), 2.13 (s, 3H), 2.40 (t, 2H), 17.8 (CH3), 19.4, 24.9, 49.5 (CH2–CH2–CH2–), 47.4,
2.38–2.73 (complicate, 8H) 4.14 (m, 1H), 7.62–7.85 53.7 (N–CH2–CH2–N), 68.5 (CH), 120–129 (Ar–C),
(m, 14H), 10. 40 (s, 1H)
168.9 (CONH), 194.3 (C=O)
3350, 3020, 2915,
1736, 1680, 1370,
1155
1.13 (q, 2H), 1.38 (t, 2H), 1.95 (s, 3H), 2.18 (s, 3H), 18.3 (CH3), 19.3, 24.9, 49.8 (CH2-CH2-CH2-), 24.7
2.35 (t, 2H), 2.42-2.75 (Complicate, 8H) 4.13 (m,
1H), 7.60-7.83 (m, 9H), 10. 42 (s, 1H)
(CH3), 47.5, 53.8 (N-CH2-CH2-N), 169.7 (CONH),
68.3 (CH), 121-129 (Ar–C), 193.5 (C=O)
3350, 3025, 2907,
1730, 1680, 1370,
1150, 1105, 1245
1.15 (q, 2H), 1.36 (t, 3H), 1.49 (t, 2H), 2.07 (s, 3H), 17.5 (CH3), 19.3, 24.9, 49.7 (CH2–CH2–CH2–), 22.6
2.15 (s, 3H), 2.36 (t, 2H), 2.40-2.78 (complicate, 8H), (CH3), 47.5, 53.8 (N–CH2–CH2–N), 59.5 (O–CH2–),
4.05 (q, 2H), 4.15 (m, 1H), 7.62–7.85 (m, 4H), 10. 23 68.5(CH), 168.9 (CONH), 122–128 (Ar–C), 194.3
(s, 1H)
1.10 (q, 2H), 1.30 (t, 6H), 1.40 (t, 2H), 2.10 (s, 3H), 17.5 (CH3), 19.3, 24.9, 49.7 (CH2–CH2–CH2–), 47.5,
2.35 (t, 2H), 2.42–2.75 (complicate, 8H), 3.85 (q, 53.8 (N–CH2–CH2–N), 59.3 (O–CH2–), 68.5 (CH),
4H), 4.12 (m, 1H), 7.62-7.85 (m, 4H), 10. 38 (s, 1H) 169.4 (CONH), 124–129 (Ar–C), 194.8 (C=O)
(C=O)
5e
3350, 3020, 2915,
1780, 1660, 1370,
1150, 1120, 1245
results were found to be in good agreement with the cal-
culated values.
presence of SSA (0.01 M) was stirred 50°C for 2 h. The
progress of reaction was monitored by TLC using 7:2:1
(benzene:ethanol:ammonia) upper layer as mobile phase.
Upon completion of reaction, the mixture was extracted
with ethyl acetate (2 9 25 ml), and the solvent was
removed. The crude product was washed with dry ether and
recrystallized from pet ether:ethyl acetate (1:1). The
product was purified by column chromatography over silica
gel using pet ether:ethyl acetate (40:60) as eluent.
Synthesis of [N4-(4-acetylamino) benzene sulfonyl)
piperazinyl-N1-propyl]-1,3-dimethyl/1-methyl-3-
phenyl/1,3-diphenyl/1-methyl-3-ethoxy/1,3-diethoxy
propane-1,3-dione 5a–e
Sodium methoxide (0.54 g, 0.01 mol) and b-diketones/
b-ketoester (0.01 mol) were placed in a dried round-bottom
flask and stirred for 1 h on a magnetic stirrer at 50°C, after
which a creamy mass was obtained. The N4-(4-acetyl-
amino) benzene sulfonyl) piperazinyl-N1-1-bromopropane
3 (3.9 g, 0.01 mol) was taken in dry toluene and added
drop by drop in above said reaction mass. The reaction
mixture was heated for 7 h at 80°C with stirring. The
progress of the reaction was monitored by TLC. After
completion of the reaction, the mixture was cooled and
toluene was removed. The reaction mixture was extracted
using chloroform and washed with water.
6-[N4-(4-Acetylamino) benzene sulfonyl) piperazinyl-N1-
propyl]-5,7-dimethyl-2,3-dihydro-1H-1,4-diazepine 6a
M.p. 145°C, yield 75%; IR (KBr): 3315 (N–H), 3010
(Ar–H), 2930 (C–H), 1700 (C=O), 1570 (C=N), 1345, 1140
(-SO2) cm-1
;
1H NMR (CDCl3): d 1.09 (quintet,
J = 7.46, 2H, CH2CH2CH2), 1.15 (triplet, J = 7.50, 2H,
CH2CH2CH2), 2.07 (s, 6H,CH3–C=N), 2.16 (s, 3H, CH3),
2.30 (triplet, J = 7.45, 2H, CH2CH2CH2–N), 3.14 (com-
plicated s, 4H,N–CH2–CH2–N), 3.45 (s, 1H, =CH–),
7.65–7.80 (m, 4H, Ar–H), 8.50 (s,1H, N–H); 13C NMR
(CDCl3): d 10.45, 16.45, 17.63, 28.20, 47.30, 48.55, 53.40,
124–128, 134.90, 164.60, 168.20; MS (m/z): 448
(M ? H?); Anal. Calcd for C22H33N5O3S: C, 59.06; H,
7.38; N, 15.66. Found: C 58.95, H 7.13, N, 15.45.
The chloroform layer was dried using anhydrous sodium
sulphate and distilled to yields the solid compound. The
product was purified by column chromatography over silica
gel using pet ether:ethyl acetate (50:50) as eluent. It was
purified by recrystallization from chloroform and ethyl
acetate. Purity of the compound was checked by TLC on
aluminium oxide 60 F254 plates (Merck) in a 7:2:1 (ben-
zene:ethanol:ammonia) upper layer using as a mobile
phase (Table 2).
6-[N4-(4-Acetylamino) benzene sulfonyl) piperazinyl-N1-
propyl]-5,7-diphenyl-2,3-dihydro-1H-1,4-diazepine 6b
M.p. 167°C, yield 73%; IR (KBr): 3325 (N–H), 3010 (Ar–
H), 2915 (C–H), 1705 (C=O), 1580 (C=N), 1355, 1145
(-SO2) cm-1; 1H NMR (CDCl3): d 1.10(quintet, J = 7.03,
2H, CH2CH2CH2), 1.13 (triplet, J = 7.25, 2H,
CH2CH2CH2), 2.15 (s, 3H, CH3), 2.32 (triplet, J = 6.85,
2H, CH2CH2CH2–N), 3.15 (complicated s, 4H,N–CH2–
Synthesis of 1H-1,4-diazepine derivatives 6a–e: general
procedure
An equimolar ratio of b-diketones/b-ketoesters (0.01 M)
5a–e, and EDA (0.01 M) in ethyl acetate (50 ml) in the
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