2H), 6.58 (brs, 1H), 7.33–7.46 (m, 6H), 7.53 (t, J ¼ 7.3 Hz, 1H),
7.75 (d, J ¼ 7.4 Hz, 2H). 13C NMR (125 MHz, CDCl3/TMS)
d (ppm): 1.5, 31.8, 34.0, 44.3, 126.1, 127.4, 128.6, 128.8, 129.0,
131.9, 135.6, 151.1, 167.8. Anal. calcd for C18H21NO (267.37): C,
80.86; H, 7.92; N, 5.24. Found: C, 80.84; H, 7.89; N, 5.23.
(KBr): n ¼ 3350, 1630, 1310 cmꢂ1. 1H NMR (500 MHz, CDCl3/
TMS) d (ppm): 2.04 (s, 3H), 6.15 (brs, 1H), 6.25 (d, J ¼ 5.0 Hz,
1H), 7.21–7.35 (m, 10H). 13C NMR (125 MHz, CDCl3/TMS)
d (ppm): 23.8, 57.4, 127.7, 127.8, 127.9, 128.8, 129.1, 141.9, 169.5.
Anal. calcd for C15H15NO (225.29): C, 79.97; H, 6.71; N, 6.22.
Found: C, 79.94; H, 6.68; N, 6.19.
5.4. N-(4-Fluorobenzyl)benzamide (d). White color, mp 114–
116 ꢁC. MS: m/z (%): 229.08 (81), 109.05 (38), 120.05 (62), 77.04
(36). IR (KBr): n ¼ 3290, 1620, 1415 cmꢂ1. 1H NMR (500 MHz,
CDCl3/TMS) d (ppm): 4.59 (d, J ¼ 4.9 Hz, 2H), 6.56 (brs, 1H),
7.01 (t, J ¼ 8.1 Hz, 2H), 7.30 (m, 2H), 7.40–7.49 (m, 3H) 7.78 (d,
J ¼ 7.1 Hz, 2H). 13C NMR (125 MHz, CDCl3/TMS) d (ppm):
43.8, 115.9, 116.1, 127.4, 129.0, 129.9, 130.0, 132.0, 134.5, 134.9.
Anal. calcd for C14H12FNO (229.25): C, 73.35; H, 5.28; N, 6.11.
Found: C, 73.33; H, 5.25; N, 6.09.
5.10. N-Benzhydrylacetamide (j). White color, mp 110–
ꢁ
111 C. MS: m/z (%): 183.15 (79), 111.06 (47), 83.09 (16), 72.08
(31). IR (KBr): n ¼ 3300, 1635, 1390 cmꢂ1. 1H NMR (500 MHz,
CDCl3/TMS) d (ppm): 1.18–1.24 (m, 4H), 1.31 (s, 9H), 1.34–1.80
(m, 6H), 1.94 (m, 1H), 5.23 (brs, 1H). 13C NMR (125 MHz,
CDCl3/TMS) d (ppm): 26.2, 29.3, 30.2, 46.7, 51.2, 176.0. Anal.
calcd for C11H21NO (183.29): C, 72.08; H, 11.55; N, 7.64. Found:
C, 72.03; H, 11.51; N, 7.62.
5.5. N-(4-Fluorobenzyl)cyclopropanecarboxamide (e). White
ꢁ
5.11. N-tert-Butylcyclohexanecarboxamide (k). White color,
mp 107–109 ꢁC. MS: m/z (%): 231.15 (83), 126.09 (37), 105.07
(24), 83.09 (44). IR (KBr): n ¼ 3320, 1640, 1430 cmꢂ1. 1H NMR
(500 MHz, CDCl3/TMS) d (ppm): 1.21–1.25 (m, 3H), 1.40–1.88
(m, 10H), 2.03–2.09 (m, 1H), 5.09–5.15 (m, 1H), 5.67 (brs, 1H),
7.23–7.34 (m, 5H). 13C NMR (125 MHz, CDCl3/TMS) d (ppm):
22.2, 26.7, 30.0, 30.1, 46.0, 48.7, 126.5, 127.7, 129.1, 143.9 and
175.5. Anal. calcd for C15H21NO (231.33): C, 77.88; H, 9.15; N,
6.05. Found: C, 77.82; H, 9.11; N, 6.04.
color, mp 117–119 C. MS: m/z (%):193.07 (base peak), 125.05
(56), 70.02 (43). IR (KBr): n ¼ 3290, 1625, 1390 cmꢂ1. 1H NMR
(500 MHz, CDCl3/TMS) d (ppm): 0.75 (dt, J ¼ 10.7, 3.5 Hz, 2H),
1.0 (dt, J ¼ 7.4, 3.0 Hz, 2H), 1.33–135 (m, 1H), 4.41 (d, J ¼ 5.7
Hz, 2H), 5.92 (brs, 1H), 6.98–7.03 (m, 2H), 7.24–7.27 (m, 2H).
13C NMR (125 MHz, CDCl3/TMS) d (ppm): 7.7, 15.2, 43.5,
115.8, 116.0, 129.8, 129.9, 134.8, 163.6, 173.9. Anal. calcd for
C11H12FNO (193.22): C, 68.38; H, 6.26; N, 7.25. Found: C,
68.34; H, 6.21; N, 7.22.
5.12. N-(1-Phenylethyl)cyclohexanecarboxamide (l). White
color, mp 147–148 ꢁC. MS: m/z (%): 239.14 (77), 167.09 (45),
5.6. N-(1-Phenylethyl)cyclopropanecarboxamide (f). White
color, mp 102–103 ꢁC. MS: m/z (%): 231.15 (69), 162.13 (51),
147.12 (20), 84.04 (28). IR (KBr): n ¼ 3300, 1635, 1390 cmꢂ1. 1H
NMR (500 MHz, CDCl3/TMS) d (ppm): 1.18–1.24 (m, 4H), 1.31
(s, 9H), 1.34–1.80 (m, 6H), 1.94 (m, 1H), 5.23 (brs, 1H). 13C
NMR (125 MHz, CDCl3/TMS) d (ppm): 7.6, 15.2, 31.8, 34.9,
44.0, 126.1, 128.1, 135.9, 151.0, 173.7. Anal. calcd for C15H21NO
(231.33): C, 77.88; H, 9.15; N, 6.05. Found: C, 77.86; H, 9.13; N,
6.04.
72.04 (14), 57.03 (54). IR (KBr): n ¼ 3300, 1635, 1380 cmꢂ1. H
1
NMR (500 MHz, CDCl3/TMS) d (ppm): 1.17 (t, J ¼ 7.5 Hz, 3H),
2.27 (q, J ¼ 2.1, 7.5 Hz, 2H), 6.15 (brs, 1H), 6.26 (d, J ¼ 8.0 Hz,
1H), 7.22 (d, J ¼ 7.1 Hz, 4H), 7.26 (t, J ¼ 7.2 Hz, 2H), 7.32 (t, J ¼
7.1 Hz, 4H). 13C NMR (125 MHz, CDCl3) d (ppm): 10.3, 30.1,
57.2, 127.7, 127.8, 128.8, 129.1, 124.1, 173.2. Anal. calcd for
C16H17NO (239.31): C, 80.30; H, 7.16; N, 5.85. Found: C, 80.26;
H, 7.11; N, 5.83.
5.7. N-(4-tert-Butylbenzyl)cyclopropanecarboxamide
(g).
5.13. N-Benzhydrylpropionamide (m). White color, mp 112–
ꢁ
White color, mp 141–142 ꢁC. MS: m/z (%): 141.11 (49), 85.04
113 C. MS: m/z (%): 191.12 (55), 100.08 (62), 91.05 (37), 72.08
(57), 58.07 (61), 44.06 (28). IR (KBr): n ¼ 3290, 1635, 1390 cmꢂ1
.
(21). IR (KBr): n ¼ 3290, 1620, 1415 cmꢂ1. 1H NMR (500 MHz,
CDCl3/TMS) d (ppm): 1.32 (s, 9H), 3.48 (s, 2H), 5.20 (brs, 1H),
7.23–7.26 (m, 3H), 7.32–7.35 (m, 2H), 13C NMR (125 MHz,
CDCl3/TMS) d (ppm): 29.1, 45.3, 51.6, 127.5, 129.3, 129.7, 135.9,
170.7. Anal. calcd for C12H17NO (191.27): C, 75.35; H, 8.96; N,
7.32. Found: C, 75.31; H, 8.91; N, 7.29.
1H NMR (500 MHz, CDCl3/TMS) d (ppm): 0.69 (dt, J ¼ 10.7,
3.5 Hz, 2H), 0.92 (dt, J ¼ 7.1, 3.0 Hz, 2H), 1.25–130 (m, 1H), 1.38
(s, 9H), 5.53 (brs, 1H). 13C NMR (125 MHz, CDCl3/TMS)
d (ppm): 7.0, 15.8, 29.4, 15.6, 173.0. Anal. calcd for C8H15NO
(141.21): C, 68.04; H, 10.71; N, 9.92. Found: C, 68.01; H, 10.68;
N, 9.90.
Acknowledgements
5.8. N-tert-Butylcyclopropanecarboxamide (h). White color,
mp 123–125 ꢁC. MS: m/z (%):259.06 (83), 225.11 (37), 183.23 (21)
168.21 (60), 93.50 (34). IR (KBr): n ¼ 3230, 1635, 1395 cmꢂ1. 1H
NMR (500 MHz, CDCl3/TMS) d (ppm): 4.19 (s, 2H), 6.26 (d,
1H, J ¼ 8.2 Hz), 7.19 (brs, 1H), 7.24 (d, J ¼ 4.0 Hz, 4H), 7.29 (t,
J ¼ 7.2 Hz, 2H), 7.35 (t, J ¼ 7.2 Hz, 4H). 13C NMR (125 MHz,
CDCl3/TMS) d (ppm): 43.1, 57.6, 127.7, 128.2, 129.2, 141.2,
165.4. Anal. calcd for C15H14ClNO (259.73): C, 69.36; H, 5.43;
N, 5.39. Found: C, 69.30; H, 5.40; N, 5.37.
We acknowledge Shiraz University for partial support of this
work. Also, we are thankful to Dr Reza Yousefi for helpful
comments.
Notes and references
1 D. Choudhary, S. Paul, R. Gupta and J. H. Clark, Green Chem., 2006,
8, 479.
2 J. A. Melero, R. V. Grieken and G. Morales, Chem. Rev., 2006, 106,
3790.
3 B. Karimi and D. Zareyee, Org. Lett., 2008, 10, 3989.
4 W. M. Van Rhijn, D. E. De Vos, B. F. Sels, W. D. Bossaert and
P. A. Jacobs, Chem. Commun., 1998, 317.
5.9. N-Benzhydryl-2-chloroacetamide (i). White color, mp
144–145 ꢁC. MS: m/z (%): 225.12 (70), 168.10 (38), 59.04 (52). IR
12850 | J. Mater. Chem., 2011, 21, 12842–12851
This journal is ª The Royal Society of Chemistry 2011