COLLOID AND NANO-SIZED CATALYSTS IN ORGANIC SYNTHESIS: X.
825
Yield 11.5 g (0.1 mol, 94%), bp 220–222°C (bp 222°C
[35]). Н NMR spectrum, δ, ppm: 1.46–1.66 m (6Н,
3CH2), 3.31 d. t (4Н, 2CH2N, J 11, 26 Hz), 7.80 s (1H,
СHО).
N-Butylphthalimide (VIIIc) was prepared similarly
to compound VIa according to procedure b from 6 g
(0.041 mol) of imide VIIb, 0.06 g (0.001 mol) of
copper nanoparticles, and 7.3 g (0.1 mol) of amine Vf
for 3 h. Yield 5.9 g (0.029 mol, 70%), mp 28–31°C
(mp 29–33°C [38]). 1Н NMR spectrum, δ, ppm: 0.89 t
(3Н, СН3, J 14.7 Hz), 1.23–1.34 m (2Н, CH2), 1.50–
1.60 m (2Н, CH2), 3.51 t (2Н, CH2N, J 14.4 Hz), 7.60–
7.69 m (4H, С6Н4).
1
N-Formylmorpholine (VId). a. Synthesis was
performed similarly according to procedure a from 5 g
(0.11 mol) of formamide, 0.9 g (0.005 mol) of
CuCl2·2H2O, and 9.6 g (0.11 mol) of amine Vd. Yield
10.7 g (0.093 mol, 85%), bp 238–241°C (bp 239–241°C,
mp 20–23°С [36]). 1Н NMR spectrum, δ, ppm: 3.34 d.t
(4Н, 2CH2N, J 9.3, 15.6 Hz), 3.51 d. t (4Н, 2CH2О, J
9.3, 15.8 Hz), 7.89 s (1H, СHО).
ACKNOWLEDGMENTS
This work was financially supported by the Ministry
of Education and Science of Russian Federation in the
frame of the basic part of governmental contract
no. 2014/16 (project no. 2679).
b. Synthesis was performed similarly to compound
VIa according to procedure a from 5 g (0.067 mol) of
dimethylformamide, 0.51 g (0.003 mol) of CuCl2·
2H2O, and 5.8 g (0.067 mol) of morpholine at 60°C for
1 h. Yield 6.6 g (0.057 mol, 85%), bp 239–241°C.
REFERENCES
N-Cyclohexylacetamide (VIe) was prepared
similarly to compound VIa according to procedure a
from 5 g (0.085 mol) of acetamide, 0.51 g (0.003 mol)
of CuCl2·2H2O, and 8.2 g (0.085 mol) of amine Va at
60°C; reaction time 1 h. Yield 10.3 g (0.073 mol,
86%), bp 289–292°С (bp 291–293°С [32]).
1. Mokhov, V.M., Popov, Yu.V., and Nebykov, D.N.,
Russ. J. Gen. Chem., 2014, vol. 84, no. 11, p. 2073.
DOI: 10.1134/S1070363214110036.
2. Weygand-Hilgetag, Metody eksperimenta v organi-
cheskoi khimii (Methods of Experiment in Organic
Chemistry). Мoscow: Khimiya, 1968. 944 p.
3. Hofmann, A.W., Chem. Ber., 1882, vol. 15, p. 977.
DOI: 10.1002/cber.188201501202.
4. Noybs, W.A., and Goebel, W.F., J. Am. Chem. Soc.,
1922, vol. 44, no. 10, p. 2286. DOI: 10.1021/ja01431a026.
5. Allen, C.L., and Williams, J.M.J., Chem. Soc. Rev.,
1-(3-Methylbutanoyl)piperidine (VIf) was prepared
similarly to compound VIa according to procedure b
from 5 g (0.05 mol) of compound IVd, 0.06 g
(0.001 mol) of copper nanoparticles, and 4.2 g
(0.05 mol) of amine Vc at 80–100°C for 3 h. Yield 7.2 g
2011, vol. 40, p. 3405. DOI: 10.1039/C0CS00196A.
1
(0.043 mol, 85%), bp 142–145°С (20 mmHg). Н
6. Chaudhari, P.S., Salim, S.D., Sawant, R.V., and
Akamanchi, K.G., Green Chem., 2010, vol. 12, p. 1707.
DOI: 10.1039/C0GC00053A.
7. Komura, K., Nakano, Yu., and Koketsu, M., Green
Chem., 2011, vol. 13, p. 828. DOI: 10.1039/C0GC00673D.
NMR spectrum, δ, ppm: 0.87 m (6Н, 2CH3), 1.59 s
(2Н, CH2), 1.58 d (2Н, CH2, J 4.2 Hz), 2.06 m (2H,
CH2СO), 3.38 d. t [4H, (CH2)2N, J 27.2, 9.6 Hz].
N-(Cyclohexyl)succinimide (VIIIa) was prepared
similarly to compound VIa according to procedure b
from 5 g (0.05 mol) of imide VIIa, 0.06 g (0.001 mol)
of copper nanoparticles, and 7.9 g (0.08 mol) of amine
Va for 2 h. Yield 6.9 g (0.038 mol, 76%), mp 165–
166°C, bp 139–142°C (20 mmHg) (mp 164–166°C, bp
8. Starkov, P., and Sheppard, T.D., Org. Biomol. Chem.,
2011, vol. 9, p. 1320. DOI: 10.1039/C0OB01069C.
9. Allen, C.L., Chhatwal, A.R, and Williams, J.M.J.,
Chem. Commun., 2012, vol. 48, p. 666. DOI: 10.1039/
C1CC15210F.
10. Grosjean, Ch., Parker, J., Thirsk, C., and Wright, A.R.,
Org. Proc. Res. Dev., 2012, vol. 16, p. 781. DOI:
10.1021/op400011s.
11. Wang, Ch., Yu, H-Zh., Fu, Y., and Guob, Q.-X., Org.
Biomol. Chem., 2013, vol. 11, p. 2140. DOI: 10.1039/
c3ob27367a.
1
322.7°C (760 mmHg) [36]). Н NMR spectrum, δ,
ppm: 1.17–2.13 m (10Н, 5СН2), 2.49 s [4Н, 2CH2С(О)],
3.79 m (1Н, CHN).
N-Benzylsuccinimide (VIIIb) was prepared similarly
to compound VIa according to procedure b from 5 g
(0.05 mol) of imide VIIa, 0.06 g (0.001 mol) of copper
nanoparticles, and 9.6 g (0.09 mol) of amine Ve at 50°C
for 3 h. Yield 7 g (0.037 mol, 74%), mp 99–100°C (mp
98–99°C [37]). 1Н NMR spectrum, δ, ppm: 2.52 s [4Н,
2CH2С(О)], 4.48 s (2Н, CH2N), 7.14–7.29 m (5Н, С6Н5).
12. Gernigon, N., Al-Zoubi Raed, M., and Hall, D.G.,
J. Org. Chem., 2012, vol. 77, p. 8386. DOI: 10.1021/
jo3013258.
13. Ghosh, S., Bhaumik, A., Mondal, J., Mallik, A.,
Sengupta (Ban-dyopadhyay), S., and Mukhopadhyay, Ch.,
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 4 2015