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M. Sharma, S.M. Ray / European Journal of Medicinal Chemistry 43 (2008) 2092e2102
1
cmꢀ1; H NMR d (ppm) (CDCl3): 1.32 (s, CH3, 9H), 1.81,
2.38 (m, CH2, 2H), 2.25, 2.52 (dd, CH2, 2H), 2.91 (m, CH2,
2H), 3.60 (qn, CH, 1H), 3.83 (s, OCH3, 3H), 3.85 (s, OCH3,
3H), 5.31 (s, NH, 1H), 6.76 (s, ArH, 1H), 6.77 (s, ArH, 1H);
MS (m/z): 291 [Mþ]. Anal. Calcd for C17H25NO3: C, 70.07;
H, 8.65; N, 4.81. Found: C, 69.87; H, 8.68; N, 4.82.
(m, CH2, 4H), 1.71(m, CH2, 4H), 1.79, 2.30 (m, CH2, 2H),
2.19, 2.46 (dd, CH2, 2H), 2.88 (m, CH2, 2H), 3.58 (qn, CH,
1H), 3.65 (qn, CH, 1H), 3.82 (s, OCH3, 3H), 3.84 (s, OCH3,
3H), 5.29 (s, NH, 1H), 6.76 (s, ArH, 1H), 6.77 (s, ArH, 1H);
MS (m/z): 317 [Mþ]. Anal. Calcd for C19H27NO3: C, 71.89;
H, 8.57; N, 4.41. Found: C, 71.86; H, 8.58; N, 4.42.
5.1.6.10. 2-(5,6-Dimethoxy-2,3-dihydro-1H-inden-1-yl)-N-pen-
tylacetamide (7j). Yield 65.1% (cyclohexane); mp 102e
103 ꢂC; IR: 3319 (NH), 1646 (C]O), 1268, 1086 (OCH3)
5.1.6.15. N-Benzyl-2-(5,6-dimethoxy-2,3-dihydro-1H-inden-1-
yl)acetamide (7o). Yield 77.4% (dil. alcohol); mp 146e
147 ꢂC; IR: 3333 (NH), 1643 (C]O), 1272, 1084 (OCH3)
1
1
cmꢀ1; H NMR d (ppm) (CDCl3): 0.98 (t, CH3, 3H), 1.30
cmꢀ1; H NMR d (ppm) (CDCl3): 1.80, 2.48 (m, CH2, 2H),
(m, CH2, 4H), 1.51 (qn, CH2, 2H), 1.76, 2.24 (m, CH2,
2H), 2.27, 2.53 (dd, CH2, 2H), 2.86 (m, CH2, 2H), 3.24 (t,
CH2, 2H), 3.58 (qn, CH, 1H), 3.84 (s, OCH3, 3H), 3.86
(s, OCH3, 3H), 5.41 (s, NH, 1H), 6.76 (s, ArH, 1H), 6.77
(s, ArH, 1H); MS (m/z): 305 [Mþ]. Anal. Calcd for
C18H27NO3: C, 70.79; H, 8.91; N, 4.59. Found: C, 70.91;
H, 8.89; N, 4.60.
2.36, 2.57 (dd, CH2, 2H), 2.88 (m, CH2, 2H), 3.63 (qn, CH,
1H), 3.81 (s, OCH3, 3H), 3.83 (s, OCH3, 3H), 4.46 (s, Bnz
CH2, 2H), 5.71 (s, NH, 1H), 6.74 (s, ArH, 1H), 6.75 (s,
ArH, 1H), 7.26 (m, ArH, 5H); MS (m/z): 325 [Mþ]. Anal.
Calcd for C20H23NO3: C, 73.82; H, 7.12; N, 4.30. Found: C,
73.91; H, 7.14; N, 4.31.
5.1.6.16. 1-[(5,6-Dimethoxy-2,3-dihydro-1H-inden-1-yl)acetyl]-
pyrrolidine (7p). Yield 64.3% (ethyl acetate and n-hexane);
mp 114e115 ꢂC; IR: 1643 (C]O), 1275, 1086 (OCH3)
5.1.6.11. 2-(5,6-Dimethoxy-2,3-dihydro-1H-inden-1-yl)-N-hex-
ylacetamide (7k). Yield 57.9% (cyclohexane); mp 94e
95 ꢂC; IR: 3323 (NH), 1648 (C]O), 1267, 1083 (OCH3)
1
cmꢀ1; H NMR d (ppm) (CDCl3): 1.97 (m, CH2, 4H), 1.81,
1
cmꢀ1; H NMR d (ppm) (CDCl3): 0.98 (t, CH3, 3H), 1.31
2.29 (m, CH2, 2H), 2.31, 2.57 (dd, CH2, 2H), 2.84 (m,
CH2, 2H), 3.46 (t, CH2, 4H), 3.59 (qn, CH, 1H), 3.84 (s,
OCH3, 3H), 3.86 (s, OCH3, 3H), 6.76 (s, ArH, 1H), 6.77
(s, ArH, 1H); MS (m/z): 289 [Mþ]. Anal. Calcd for
C17H23NO3: C, 70.56; H, 8.01; N, 4.84. Found: C, 70.33;
H, 8.03; N, 4.85.
(m, CH2, 6H), 1.53 (qn, CH2, 2H), 1.78, 2.24 (m, CH2,
2H), 2.26, 2.52 (dd, CH2, 2H), 2.86 (m, CH2, 2H), 3.20 (t,
CH2, 2H), 3.60 (qn, CH, 1H), 3.84 (s, OCH3, 3H), 3.86
(s, OCH3, 3H), 5.39 (s, NH, 1H), 6.75 (s, ArH, 1H), 6.76
(s, ArH, 1H); MS (m/z): 319 [Mþ]. Anal. Calcd for
C19H29NO3: C, 71.44; H, 9.115; N, 4.38. Found: C, 71.60;
H, 9.14; N, 4.40.
5.1.6.17. 1-[(5,6-Dimethoxy-2,3-dihydro-1H-inden-1-yl)acetyl]-
piperidine (7q). Yield 57.5% (chloroform); mp 101e102 ꢂC;
5.1.6.12. N-Cyclopropyl-2-(5,6-dimethoxy-2,3-dihydro-1H-in-
den-1-yl)acetamide (7l). Yield 62.7% (ethyl acetate); mp
128e129 ꢂC; IR: 3316 (NH), 1643 (C]O), 1267, 1090
IR: 1646 (C]O), 1268, 1089 (OCH3) cmꢀ1 1H NMR
;
d (ppm) (CDCl3): 1.65 (m, CH2, 6H), 1.75, 2.45 (m, CH2,
2H), 2.72, 2.46 (dd, CH2, 2H), 2.88 (m, CH2, 2H), 3.37
(t, CH2, 4H), 3.66 (qn, CH, 1H), 3.84 (s, OCH3, 3H), 3.86
(s, OCH3, 3H), 6.76 (s, ArH, 1H), 6.77 (s, ArH, 1H); MS
(m/z): 303 [Mþ]. Anal. Calcd for C18H25NO3: C, 71.26; H,
8.31; N, 4.62. Found: C, 71.45; H, 8.33; N, 4.64.
(OCH3), 1003 (cyclopropyl) cmꢀ1
;
1H NMR d (ppm)
(CDCl3): 0.45 (m, CH2, 4H), 1.76, 2.22 (m, CH2, 2H), 2.19,
2.46 (dd, CH2, 2H), 2.41 (m, CH, 1H), 2.88 (m, CH2, 2H),
3.60 (qn, CH, 1H), 3.82 (s, OCH3, 3H), 3.84 (s, OCH3, 3H),
5.37 (s, NH, 1H), 6.76 (s, ArH, 1H), 6.77 (s, ArH, 1H); MS
(m/z): 275 [Mþ]. Anal. Calcd for C16H21NO3: C, 69.79; H,
7.69; N, 5.09. Found: C, 69.80; H, 7.70; N, 5.10.
5.1.6.18. 1-[(5,6-Dimethoxy-2,3-dihydro-1H-inden-1-yl)acetyl]-
piperazines (7r). Yield 63.7% (ethyl acetate and n-hexane);
mp 212e213 ꢂC; IR: 3345 (NH of piperazine), 1645
;
(C]O), 1269, 1087 (OCH3) cmꢀ1 1H NMR d (ppm)
(CDCl3): 1.83, 2.26 (m, CH2, 2H), 2.13 (s, NH 1H), 2.79
(t, CH2, 4H), 2.23, 2.50 (dd, CH2, 2H), 2.88 (m, CH2,
2H), 3.33 (t, CH2, 4H), 3.60 (qn, CH, 1H), 3.84 (s, OCH3,
3H), 3.86 (s, OCH3, 3H), 6.76 (s, ArH, 1H), 6.77 (s, ArH,
1H); MS (m/z): 304 [Mþ]. Anal. Calcd for C17H24N2O3:
C, 67.08; H, 7.95; N, 9.20. Found: C, 66.99; H, 7.97;
N, 9.18.
5.1.6.13. N-Cyclopentyl-2-(5,6-dimethoxy-2,3-dihydro-1H-in-
den-1-yl)acetamide (7m). Yield 72.5% (cyclohexane); mp
136e138 ꢂC; IR: 3321 (NH), 1646 (C]O), 1271, 1083
;
(OCH3) cmꢀ1 1H NMR d (ppm) (CDCl3): 1.45 (m, CH2,
4H) 1.76 (m, CH2, 4H), 1.81, 2.27 (m, CH2, 2H), 2.31, 2.54
(dd, CH2, 2H), 2.88 (m, CH2, 2H), 3.57 (qn, CH, 1H), 3.65
(qn, CH, 1H), 3.82 (s, OCH3, 3H), 3.84 (s, OCH3, 3H), 5.31
(s, NH, 1H), 6.76 (s, ArH, 1H), 6.77 (s, ArH, 1H); MS (m/
z): 303 [Mþ]. Anal. Calcd for C18H25NO3: C, 71.26; H,
8.31; N, 4.62. Found: C, 71.54; H, 8.34; N, 4.63.
5.1.6.19. 4-[(5,6-Dimethoxy-2,3-dihydro-1H-inden-1-yl)acetyl]-
morpholines (7s). Yield 61.6% (dil. alcohol); mpꢀ1137e
5.1.6.14. N-Cyclohexyl-2-(5,6-dimethoxy-2,3-dihydro-1H-inden-
1-yl)acetamide (7n). Yield 70.5% (cyclohexane); mp 152e
153 ꢂC; IR: 3327 (NH), 1645 (C]O), 1269, 1086 (OCH3)
138 ꢂC; IR: 1648 (C]O), 1270, 1081 (OCH3) cm 1H
;
NMR d (ppm) (CDCl3): 1.74, 2.43 (m, CH2, 2H), 2.68, 2.45
(dd, CH2, 2H), 2.85 (m, CH2, 2H), 3.47 (t, CH2, 4H), 3.60
(qn, CH, 1H), 3.69 (t, CH2, 4H) 3.84 (s, OCH3, 3H), 3.86
1
cmꢀ1; H NMR d (ppm) (CDCl3): 1.11 (qn, CH2, 2H), 1.35