COLLOID AND NANODIMENSIONAL CATALYSTS IN ORGANIC SYNTHESIS: VIII.
1923
Oxford: Pergamob, 1973. Translated under the title
spectrum, δ, ppm: 1.36–2.45 m (8H, 4CH2), 3.58 m
Organikum, Moscow: Mir, 2008, p. 180.
(1H, CH–N), 3.72 s (1H, NH), 6.38–6.95 m (5H, C6H5).
3. Popov, Yu.V., Mokhov, V.M., and Nebykov, D.N.,
Russ. J. Gen. Chem., 2014, vol. 84, no. 3, p. 444. DOI:
10.1134/S1070363214030062
4. Mokhov, V.M., Popov, Yu.V., and Nebykov, D.N.,
Russ. J. Gen. Chem., 2014, vol. 84, no. 4, p. 622. DOI:
10.1134/S1070363214040033
5. Korton, D.G., Haury, V.E., Davis, F.C., Mitchell, L.J.,
and Ballard, S.A., J. Org. Chem., 1954, vol. 19, no. 7,
p. 1054. DOI: 10.1021/jo01372a010.
N-Cyclohexylaniline (IId). Analogously to IIa
from a mixture of 0.3 g (0.008 mol) of sodium
borohydride, 15 mL of isopropanol, 0.5 g (0.004 mol)
of anhydrous NiCl2, and 10.4 g (0.06 mol) of ketimine
Id under bubbling of hydrogen for 8 h at 70°C 7.3 g
(0.041 mol, 69%) of amine IId was obtained, bp 165–
1
167°C (20 mmHg) (bp 167–168°C [20]). H NMR
spectrum, δ, ppm: 1.12–2.30 m (10H, 5CH2), 3.52 m
(1H, CH–N), 3.70 s (1H, NH), 6.40–6.97 m (5H, C6H5).
6. Imamoto, T., Iwadate, N., and Yoshida, K., Org. Lett.,
2006, vol. 8, no. 1, p. 2289. DOI: 10.1021/o1060546b.
4-(Methoxy)phenylaminocyclopentane (IIe). Analo-
gously to IIa from a mixture of 0.5 g (0.014 mol) of
sodium borohydride, 20 mL of isopropanol, 0.9 g
(0.007 mol) of anhydrous NiCl2, and 9.5 g (0.05 mol)
of imine Ie under bubbling of hydrogen for 10 h at 70°C
6.7 g (0.036 mol, 71%) of amine IIe was obtained, bp
7. Pickard, P.L. and Jenkins, S.H., J. Am. Chem. Soc.,
1953, vol. 75, no. 23, p. 5899. DOI: 10.1021/ja01119a035.
8. Xie, J.-H., Zhu, Sh.-F., and Zhou, Q.-L., Chem. Rev.,
2011, vol. 111, p. 1713. DOI: 10.1021/cr100218m.
9. Abdur-Rashid, K., Lough, A.J., and Morris, R.H.,
Organometallics, 2001, vol. 20, p. 1047. DOI: 10.1021/
om001054k.
10. Burling, S., Whittlesey, M.K., and Williams, J.M.J.,
Adv. Synth. Catal., 2005, vol. 347, p. 591. DOI:
10.1021/adsc.200600638.
1
179–182°C (20 mmHg). H NMR spectrum, δ, ppm:
1.19–2.68 m (8H, 4CH2), 3.34 br.s (1H, NH), 3.40 m
(1H, CHN), 3.60 s (3H, OCH3), 6.32–6.66 m (4H, Ph).
Found, %: C 74.58, H 8.49, N 7.87. C11H15NO. Cal-
culated, %: C 74.54, H 8.53, N 7.90.
11. Alonso, F., Riente, P., and Yus, M., Synlett., 2008,
no. 9, p. 1289. DOI: 10.1055/s-2008-1072748.
N-Benzylaminocyclohexane (IIf). Analogously to
IIa from a mixture of 0.5 g (0.014 mol) of sodium
borohydride, 20 mL of isopropanol, 0.9 g (0.007 mol)
of anhydrous NiCl2 and 14 g (0.075 mol) of imine If
under bubbling of hydrogen for 8 h at 70°C 10.2 g
(0.056 mol, 74%) of amine IIf was obtained, bp 168–
12. Alonso, F. and Yus, M., Chem. Soc. Rev., 2004, vol. 33,
p. 284. DOI: 10.1039/B315131J.
13. Alonso, F., Riente, P., and Yus, M., Acc. Chem. Res.,
2011, vol. 44, p. 379. DOI: 10.1021/ar1001582.
14. Hou, Y., Kondoh, H., Ohta, T., and Gao, S., Appl.
Surface Sci., 2005, vol. 241, p. 218. DOI: 10.1016/
j.apususc.2004.09.045.
1
171°C (25 mmHg). H NMR spectrum, δ, ppm: 1.03–
2.35 m (10H, 5CH2), 2.38 m (1H, CH–N), 3.05 s (2H,
CH2–N),7.05–7.22 m (5H, C6H5). Found, %: C 82.54,
H 10.15, N 7.31. C13H19N. Calculated, %: C 82.48, H
10.12, N 7.40.
15. Tee, T.-H., Bachas, L., and Bhattacharyya, D., J. Phys.
Chem., C, 2009, vol. 113, p. 9454. DOI: 10.1021/jp809098z.
16. Borodzinski, J.J. and Lasia, A., J. Appl. Electrochem.,
1994, vol. 24, p. 1267. DOI: 10.1007/BF00249892.
N-Benzylaminobutane (IIg). Analogously to IIa
from a mixture of 0.5 g (0.014 mol) of sodium
borohydride, 20 mL of tert.-butanol, 0.9 g (0.007 mol)
of anhydrous NiCl2, and 11.3 g (0.07 mol) of imine Ig
under bubbling of hydrogen for 9 h at 65°C 9.8 g
(0.06 mol, 86%) of amine IIg was obtained, nD20
1.5014 (nD20 1.5022 [21]).
17. Rahimizadeh, M., Bakhtiarpoor, Z., Eshghi, H., Pordel, M.,
and Rajabzadeh, G., Monatsh. Chem., 2009, vol. 140,
no. 12, p. 1465. DOI: 10.1007/s00706-009-0205-8.
18. Choudary, B.M., Randanath, K.V.S., Yadav, J., and
Kantam, M.L., Tetrahedron Lett., 2005, vol. 46, no. 8,
p. 1369. DOI: 10.1016/j.tetlet.2004.12.078.
19. Spravochnik khimika (Chemists Handbook), Nikol’-
skii, B.I., Ed., Leningrad: Khimiya, 1971, vol. 2, p. 424.
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RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 10 2014