Y. Kawagoe et al. / Tetrahedron 69 (2013) 3971e3977
3977
(two, s, ratio¼1:2, 1H); 13C NMR (DMSO-d6 500 MHz, TMS):
Chiralpack OD-H, Hexane/i-PrOH¼9:1, flow rate¼1.0 mL/min)
tR¼26.1 min (major, S), 23.3 min (minor, R).
d
¼23.16 and 23.99 (rotamers), 27.95 and 28.15 (rotamers), 30.06
and 31.16 (rotamers), 41.81 and 42.04 (rotamers), 46.49 and 46.67
(rotamers), 59.80 and 59.93 (rotamers), 78.46 and 78.61 (rotamers),
126.57 and 126.72 (rotamers), 126.83, 127.30 and 128.15 (rotamers),
139.63 and 153.37 (rotamers), 139.63 and 153.70 (rotamers), 172.27
and 172.47 (rotemers); HPLC (Daicel Chiralpack AD-H, Hexane/i-
PrOH¼9:1, flow rate¼0.5 mL/min) tR¼26.6 min (major, S), 14.5 min
(minor, R).
4.4.34. N-Methoxy-N-methyl-4-methoxy-benzamide. Yield:
173.7 mg (89%); colorless oil; IR: 1633 cmꢂ1 1H NMR (CDCl3
;
400 MHz, TMS):
d
¼3.34 (s, 3H), 3.55 (s, 3H), 3.83 (s, 3H), 6.90 (d, 2H,
J¼9.0 Hz), 7.72 (d, 2H, J¼9.0 Hz); 13C NMR (CDCl3 100 MHz, TMS):
d¼33.66, 55.08, 60.65, 113.03, 125.80, 130.30, 161.32, 169.14; HRMS
(ESI) (MþH)þ calcd for C10H14O3N¼196.0968, found¼196.0967.
4.4.27. N-(30-Phenylpropyl)-4-methoxybenzamide. Yield: 269.3 mg
(>99%); mp 88e89 ꢀC (lit.23 mp 88e89 ꢀC); IR: 1627, 3322 cmꢂ1; 1H
Acknowledgements
NMR (CDCl3 400 MHz, TMS):
d
¼1.92e1.97 (m, 2H), 2.69 (t, 2H,
Financial support in the form of a Grant-in-Aid for Scientific
Research (No. 20550033) from the Ministry of Education, Culture,
Sports, Science, and Technology in Japan, and Iodine Research
Project in Chiba University is gratefully acknowledged.
J¼7.4 Hz), 3.46 (dt, 2H, J¼6.8 Hz, 6.5 Hz), 3.82 (s, 3H), 6.28 (br, 1H),
6.87 (d, 2H, J¼8.3 Hz), 7.18e7.20 (m, 3H), 7.26e7.30 (m, 2H), 7.66 (d,
2H, J¼8.3 Hz); 13C NMR (CDCl3 100 MHz, TMS):
¼31.12, 33.45,
d
39.68, 55.28, 113.54, 125.91, 126.86, 128.31, 128.44, 128.56, 141.49,
161.93, 166.92.
Supplementary data
4.4.28. N-Dodecyl-4-methoxybenzamide. Yield: 277.9 mg (87%); mp
Supplementary data related to this article can be found at http://
85 ꢀC; IR: 1627, 3337 cmꢂ1; 1H NMR (CDCl3 400 MHz, TMS):
d¼0.88
(t, 3H, J¼6.8 Hz), 1.23e1.36 (br, 18 H), 1.56e1.64 (m, 2H), 3.40e3.45
(m, 2H), 3.84 (s, 3H), 6.06 (br, 1H), 6.91 (d, 2H, J¼8.8 Hz), 7.73 (d, 2H,
References and notes
J¼8.8 Hz); 13C NMR (CDCl3 100 MHz, TMS):
¼14.01, 22.44, 22.66,
d
1. (a) Ghose, A. K.; Viswanadhan, V. N.; Wendoloski, J. J. J. Comb. Chem. 1999, 1, 55;
(b) Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606.
27.03, 29.32, 29.54, 29.57, 29.61, 29.73, 31.90, 40.03, 45.55, 55.37,
113.67, 127.16, 128.56, 162.00, 166.95; HRMS (APCI) (MþH)þ calcd
for C20H34O2N¼320.2578, found¼320.2578.
2. (a) Ziegler, T. Synthesis, of Amides from Carboxylic Acid and Derivatives In. Science
of Synthesis; Weinreb, S. M., Ed.; Georg Thieme: 2005; Vol. 21, p 43; (b) Cook, G. R.
Synthesis, of Amides from Amines In. Science of Synthesis; Weinreb, S. M., Ed.;
Georg Thieme: 2005; Vol. 21, p 111; (c) Larock, R. C. Comprehensive Organic
Transformation; VCH: 1989, pp 972e976, Reviews for peptides; (d) Klausner, Y. S.;
Bodanszky, M. Synthesis 1974, 549; (e) Klausner, Y. S.; Bodanszky, M. Synthesis
1972, 453, Recent papers; (f) Luo, Q.; Lv, L.; Li, Y.; Tan, J.; Nan, W.; Hui, Q. Eur. J. Org.
Chem. 2011, 6916; (g) Tian, J.; Gao, W.; Zhou, D.; Zhang, C. Org. Lett. 2012, 14, 3020
and references are cited therein.
3. Recent reviews: (a) Ishihara, K. Tetrahedron 2009, 65, 1085; (b) Georgiou, I.;
Ilyashenko, G.; Whiting, A. Acc. Chem. Res. 2009, 42, 756; (c) Charville, H.; Jackson,
D.; Hodges, G.; Whiting, A. Chem. Commun. 2010,1813; (d) Allen, C. L.; Williams, J.
M. J. Chem. Soc. Rev. 2011, 40, 3405; (e) See Ref. 3d, and references are cited
therein. Papers; (f) Ishihara, K.; Ohara, S.; Yamamoto, H. Organic Syntheses; 2002;
Collect. Vol. No. 79 176; (g) Tang, P. Organic Syntheses; 2005; Collect. Vol. No. 81
262; (h) Gernigon, N.; Al-Zoubi, R. M.; Hall, D. G. J. Org. Chem. 2012, 77, 8386; (i)
Hosseini-Sarvari, M.; Sodagar, E.; Doroodmand, M. M. J. Org. Chem. 2011, 76, 2853;
(j) Komura, K.; Nakano, Y.; Koketsu, M. Green Chem. 2011, 13, 828.
4. (a) Lundberg, H.; Tinnis, F.; Adolfsson, H. Synlett 2012, 2201; (b) Lundberg, H.;
Tinnis, F.; Adolfsson, H. Chem.dEur. J. 2012, 18, 3822; (c) Tinnis, F.; Lundberg, H.;
Adolfsson, H. Adv. Synth. Catal. 2012, 354, 2531; (d) Ghosh, S.; Bhaumik, A.;
Mondal, J.; Mallik, A.; Sengupta, S.; Mukhopadhyay, C. Green Chem. 2012, 14,
3220 and references are cited therein.
5. (a) Barstow, L. E.; Hruby, V. J. J. Org. Chem. 1971, 36, 1305; (b) Ogata, N.; Sanui, K.;
Tan, S. Polym. J. 1984, 16, 569; (c) Harrison, C. R.; Hodge, P.; Hunt, B. J.; Khoshdel,
E.; Richardson, G. J. Org. Chem. 1983, 48, 3721; (d) Buchstaller, H.; Ebert, H. M.;
Anlauf, U. Synth. Commun. 2001, 31, 1001.
4.4.29. N-Cyclohexyl-4-methoxybenzamide. Yield: 228.6 mg ꢂ(918%);
mp 153e155 ꢀC (lit.24 mp 159e162 ꢀC); IR: 1624, 3302 cm
;
1H
NMR (CDCl3 400 MHz, TMS):
d
¼1.19e1.27 (m, 3H), 1.36e1.48 (m,
2H), 1.61e1.67 (m, 1H), 1.72e1.78 (m, 2H), 2.01e2.04 (m, 2H), 3.84
(s, 3H), 3.93e3.99 (m, 1H), 5.87 (br, 1H), 6.91 (d, 2H, J¼8.6 Hz), 7.72
(d, 2H, J¼8.7 Hz); 13C NMR (CDCl3 100 MHz, TMS):
¼24.92, 25.60,
d
33.32, 48.55, 55.39, 113.66, 127.38, 128.55, 161.98, 166.08.
4.4.30. N-(4-Methoxybenzoyl)piperidine. Yield: 201.7 mg (92%);
colorless oil; IR: 1607 cmꢂ1 1H NMR (CDCl3 400 MHz, TMS):
;
d
¼1.56e1.58 (br, 4H), 1.65e1.67 (br, 2H), 3.54e3.63 (br, 4H), 3.81 (s,
3H), 6.89 (d, 2H, J¼9.3 Hz), 7.36 (d, 2H, J¼9.3 Hz); 13C NMR (CDCl3
100 MHz, TMS):
d¼24.48, 25.61, 43.64, 48.84, 55.18, 113.45, 128.41,
128.68, 160.33, 170.12; HRMS (ESI) (MþH)þ calcd for
C14H18O2N¼220.1332, found¼220.1326.
4.4.31. N-(4-Methoxybenzoyl)morpholine. Yield: 219.0 mg (99%);
colorless oil; IR: 1607 cmꢂ1 1H NMR (CDCl3 400 MHz, TMS):
;
6. Kosal, A. D.; Wilson, E. E.; Ashfeld, B. L. Angew. Chem., Int. Ed. 2012, 51, 12036.
7. (a) Imura, Y.; Shimojuh, N.; Kawano, Y.; Togo, H. Tetrahedron 2010, 66, 3421; (b)
Shimojuh, N.; Imura, Y.; Moriyama, K.; Togo, H. Tetrahedron 2011, 67, 951; (c)
Imura, Y.; Shimojuh, N.; Moriyama, K.; Togo, H. Tetrahedron 2012, 68, 2319.
8. Katritzky, A. R.; Singh, S. K.; Cai, C. J. Org. Chem. 2006, 71, 3375.
d
¼3.64e3.69 (m, 8H), 3.82 (s, 3H), 6.91 (d, 2H, J¼8.6 Hz), 7.38 (d, 2H,
J¼8.6 Hz); 13C NMR (CDCl3 125 MHz, TMS):
¼42.86, 48.50, 55.09,
d
66.62, 113.51, 127.01, 128.95, 160.62, 170.13; HRMS (ESI) (MþH)þ
calcd for C12H16O3N¼222.1125, found¼222.1120.
9. Petricci, E.; Mugnaini, C.; Radi, M.; Corelli, F.; Botta, M. J. Org. Chem. 2004, 69, 7880.
10. Cui, X.; Zhang, Y.; Shi, F.; Deng, Y. Chem.dEur. J. 2011, 17, 1021.
11. Mamat, C.; Flemming, A.; Kockerling, M.; Steinbach, J. Synthesis 2009, 3311.
12. Clark, C. R.; Davenport, T. W. J. Med. Chem. 1987, 30, 1214.
13. Ramontian, E. Acad. Rep. Populare Romine, Filiala Cluj, Studii Cercetari Chem.
1963, 14, 327.
4.4.32. N-(40-Methylphenyl)-4-methoxybenzamide. Yield: 214.7 mg
€
(89%); mp 150 ꢀC (lit.25 mp 153.1e153.8 ꢀC); IR: 1651, 3340 cmꢂ1
;
1H NMR (CDCl3 400 MHz, TMS):
d
¼2.33 (s, 3H), 3.86 (s, 3H), 6.96 (d,
2H, J¼8.8 Hz), 7.15 (d, 2H, J¼8.2 Hz), 7.50 (d, 2H, J¼8.2 Hz), 7.70 (br,
14. Roberts, B.; Liptrot, D.; Alcaraz, L.; Luker, T.; Stoks, M. L. Org. Lett. 2010, 12, 4280.
15. Gertler, S.; Haller, H. J. Am. Chem. Soc. 1942, 64, 1741.
1H), 7.82 (d, 2H, J¼8.8 Hz); 13C NMR (CDCl3 100 MHz, TMS):
€
16. Pigulla, J.; Roder, E. Arch. Pharm. (Weinheim, Ger.) 1979, 312, 12.
d
¼20.88, 55.43, 113.89, 120.26, 127.24, 128.86, 129.52, 133.95,
17. Saito, Y.; Ouchi, H.; Takahata, H. Tetrahedron 2008, 64, 11129.
18. Chen, C.; Ho, J.; Chang, N. Tetrahedron 2008, 64, 10350.
19. D’Oca, C. R.; Coelho, T.; Marinho, T. G.; Hack, C. R.; Duarte, R. C.; da Silva, P. A.;
D’Oca, M. G. Bioorg. Med. Chem. Lett. 2010, 20, 5255.
20. Gooben, L. J.; Ohlmann, D.; Lange, P. P. Synthesis 2009, 160.
21. Yokoyama, A.; Ashida, K.; Tanaka, H. Chem. Pharm. Bull. 1964, 6, 690.
22. Gryko, D.; Lipinski, R. Eur. J. Org. Chem. 2006, 17, 3864.
23. Xing, D.; Xu, X.; Yang, L. Synthesis 2009, 3399.
24. Kanga, D. H.; Jooa, T. Y.; Chavasiric, W.; Janga, D. O. Tetrahedron 2007, 48, 285.
25. Shi, F.; Li, J.; Li, C.; Ji, X. Tetrahedron Lett. 2010, 51, 6049.
26. Kasashima, Y.; Uzawa, A.; Hashimoto, K.; Yokoyama, Y.; Mino, T.; Sakamoto, M.;
Fujita, T. J. Oleo Sci. 2010, 59, 607.
135.55, 162.36, 165.18.
4.4.33. N-(1-Phenylethyl)-4-methoxybenzamide. Yield: 224.7 mg
(88%); mp 132 ꢀC (lit.26 mp 131e132 ꢀC); IR: 1625, 3339 cmꢂ1 1H
;
NMR (CDCl3 400 MHz, TMS):
d
¼1.60 (d, 3H, J¼6.8 Hz), 3.84 (s, 3H),
5.30e5.37 (m, 1H), 6.23 (br, 1H), 6.91 (d, 2H, J¼8.6 Hz), 7.26e7.30
(m, 1H), 7.33e7.41 (m, 4H), 7.74 (d, 2H, J¼8.6 Hz); 13C NMR (CDCl3
100 MHz, TMS):
126.82, 127.40, 128.71, 143.28, 162.15, 166.15; HPLC (Daicel
d
¼21.76, 49.08, 55.40, 113.71, 125.92, 126.25,