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OLEINIK et al.
Table 2. 1H NMR spectra of 2-cycloalkylanilines X XIII
Comp.
no.
, ppm (J, Hz)
Xa
1.50 2.05 m (8H, 4CH2), 2.90 m (1H, CH), 3.40 br.s (2H, NH2), 6.44 d.d (1H, H6, J1 8, J2 2), 6.57 t.d (1H,
H5, J1 8, J2 2), 6.84 t.d (1H, H4, J1 8, J2 2), 6.95 d.d (1H, H3, J1 8, J2 2)
1.45 1.97 m (8H, 4CH2), 2.06 s (3H, CH3), 2.80 m (1H, CH), 3.39 br.s (2H, NH2), 6.49 t (1H, H4, J 8), 6.74 d
(1H, H5, J 8), 6.84 d (1H, H3, J 8)
Xb
Xc
Xd
1.45 1.98 m (8H, 4CH2), 2.03 s (3H, CH3), 2.15 s (3H, CH3), 2.85 m (1H, CH), 3.27 br.s (2H, NH2), 6.57 s
(1H, H3), 6.64 s (1H, H5)
1.45 2.09 m (8H, 4CH2), 2.88 m (1H, CH), 4.05 br.s (2H, NH2), 6.52 t (1H, H4, J 8), 6.89 d.d (1H, H3, J1 8,
J2 2), 7.00 d.d (1H, H5, J1 8, J2 2)
Xe
Xf
1.48 2.06 m (8H, 4CH2), 2.94 m (1H, CH), 3.61 br.s (2H, NH2), 3.75 c (3H, OCH3), 6.46 6.64 m (3H, H3,4,5
)
1.30 t (3H, OCH2CH3, J 7), 1.38 1.97 m (8H, 4CH2), 2.86 m (1H, CH), 3.19 br.s (2H, NH2), 3.82 q (2H,
OCH2CH3, J 7), 6.56 s (1H, H3), 6.37 d (2H, H5,6, J 6)
Xg
Xh
1.52 2.08 m (16H, 8CH2), 2.90 m (2H, 2CH), 3.54 br.s (2H, NH2), 6.54 t (1H, H4, J 8), 6.83 d (2H, H3,5, J 8)
1.31 t (3H, OCH2CH3, J 7), 1.40 2.05 m (16H, 8CH2), 2.91 m (2H, 2CH), 3.20 br.s (2H, NH2), 3.84 q (2H,
OCH2CH3, J 7), 6.42 s (2H, H3,5
)
XIa
XIb
XIc
1.10 1.90 m (10H, 5CH2), 2.35 m (1H, CH), 3.38 br.s (2H, NH2), 6.47 d.d (1H, H6, J1 8, J2 2), 6.63 t.d (1H,
H5, J1 8, J2 2), 6.84 t.d (1H, H4, J1 8, J2 2), 6.92 d.d (1H, H3, J1 8, J2 2)
1.15 1.95 m (10H, 5CH2), 2.11 s (3H, CH3), 2.38 m (1H, CH), 3.35 br.s (2H, NH2), 6.51 t (1H, H4, J 8),
6.76 d (1H, H5, J 8), 6.83 d (1H, H3, J 8)
1.10 1.90 m (10H, 5CH2), 2.04 s (3H, CH3), 2.14 s (3H, CH3), 2.52 m (1H, CH), 3.24 br.s (2H, NH2), 6.41 s
(1H, H3), 6.59 s (1H, H5)
XIg
XIIa
XIIb
1.10 2.00 m (20H, 10CH2), 2.38 m (2H, 2CH), 3.47 br.s (2H, NH2), 6.58 t (1H, H4, J 8), 6.80 d (2H, H3,5, J 8)
1.30 1.80 m (14H, 7CH2), 2.65 m (1H, CH), 3.37 br.s (2H, NH2), 6.80 7.05 m (4H, H3,4,5,6
)
1.35 1.80 m (14H, 7CH2), 2.03 s (3H, CH3), 2.61 m (1H, CH), 3.35 br.s (2H, NH2), 6.49 t (1H, H4, J 8),
6.71 d (1H, H5, J 8), 6.81 d (1H, H3, J 8)
XIIc
1.45 1.90 m (14H, 7CH2), 2.03 s (3H, CH3), 2.14 s (3H, CH3), 2.61 m (1H, CH), 3.39 br.s (2H, NH2), 6.55 s
(1H, H3), 6.60 s (1H, H5)
XIIIa 1.15 1.80 m (22H, 11CH2), 2.72 m (1H, CH), 3.48 br.s (2H, NH2), 6.49 d.d (1H, H6, J1 8, J2 2), 6.60 t.d (1H,
H5, J1 8, J2 2), 6.84 t.d (1H, H4, J1 8, J2 2), 6.95 d.d (1H, H3, J1 8, J2 2)
XIIIb 1.15 1.85 m (22H, 11CH2), 2.38 s (3H, CH3), 2.71 m (1H, CH), 3.35 br.s (2H, NH2), 6.50 t (1H, H4, J 7),
6.73 d (1H, H5, J 7), 6.82 d (1H, H3, J 7)
XIIIc 1.18 1.82 m (22H, 11CH2), 2.05 s (3H, CH3), 2.16 s (3H, CH3), 2.69 m (1H, CH), 3.48 br.s (2H, NH2), 6.58 s
(1H, H3), 6.62 s (1H, H5)
XV in 30 ml of methanol and Raney nickel prepared
from 5 g of a nickel aluminum alloy (1:1) were
placed into a 100-ml stainless-steel autoclave. The
mixture was hydrogenated with hydrogen at 10
40 atm and 30 50 C for 24 h. The catalyst was fil-
tered off, the methanol was removed from the filtrate
on a rotary evaporator at a bath temperature of 45 C,
and the residue was distilled at 1 mm Hg.
REFERENCES
1. Britovsek, G.J.P., Gibson, V.C., and Vass, D.F.,
Angew. Chem., Int. Ed. Engl., 1999, vol. 38, no. 4,
p. 429.
2. Ittel, S.D., Johnson, L.K., and Brookhart, M.J., Chem.
Rev., 2000, vol. 100, no. 4, p. 1169.
3. Gibson, V.C. and Spitzmesser, S.K., Chem. Rev.,
2003, vol. 103, no. 1, p. 283.
ACKNOWLEDGMENTS
4. Johnson, L.K., Killian, C.M., and Brookhart, M.,
The work was financially supported by the Siberian
Branch of the Russian Academy of Sciences (integra-
tion project no. 16) and the Ministry of Industry,
Science and Technologies of the Russian Federation
(State Contract no. 41.015. 1.1.2455).
J. Am. Chem. Soc., 1995, vol. 117, no. 23, p. 6414.
5. Johnson, L.K., Mecking, S., and Brookhart, M.,
J. Am. Chem. Soc., 1996, vol. 118, no. 1, p. 267.
6. Killian, C.M., Tempel, D.J., Johnson, L.K., and
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 9 2004