LEONOVA et al.
1708
13.98, 27.73, 27.96, 28.25, 32.62, 33.48, 35.29, 36.17,
40.38, 40.95, 56.58. Mass spectrum, m/z (Irel, %): 165
(16), 122 (4), 94 (100), 77 (7), 57 (14), 41 (9), 28 (11).
Found, %: C 65.58; H 9.90; N 6.89. C11H20ClN. Calcu-
lated, %: C 65.49; H 9.99; N 6.94. M 201.73.
6.9 Hz), 0.95 s (3H, CH3), 1.05‒1.98 m (13H, CH,
CH2, Ad), 8.37 br.s (3H, NH3+). 13C NMR spectrum, δC,
ppm: 13.51, 23.59, 28.53, 28.96, 33.98, 34.35, 35.13,
39.45, 39.78, 39.87, 41.83, 56.96. Mass spectrum, m/z
(Irel, %): 179 (20), 164 (3), 122 (30), 108 (95), 93 (10),
77 (5), 55 (6). Found, %: C 66.91; H 10.35; N 6.72.
C12H22ClN. Calculated, %: C 66.80; H 10.28; N 6.49.
M 215.76.
cis/trans-4-Methyladamantan-1-amine hydro-
chloride (6b). Yield 11%, white crystals, mp >300°C.
3
1H NMR spectrum, δ, ppm: 0.78 d (3H, CH3, J =
Homoadamantan-3-amine hydrochloride (12a).
Yield 77%, white crystals, mp >330°C (from aceto-
nitrile) [51].
7.9 Hz), 1.36‒2.12 m (14H, CH, CH2, Ad), 8.49 br.s
(3H, NH3+). 13C NMR spectrum, δC, ppm: 18.75, 19.53,
27.73, 27.95, 28.21, 32.53, 33.57, 35.28, 36.17, 40.07,
41.13, 52.06, 52.53. Mass spectrum, m/z (Irel, %): cis
isomer: 165 (14), 94 (100), 77 (5), 58 (21), 41 (7), 28
(9); trans isomer: 165 (16), 94 (100), 77 (5), 57 (6), 28
(7). Found, %: C 65.59; H 9.92; N 6.99. C11H20ClN.
Calculated, %: C 65.49; H 9.99; N 6.94. M 201.73.
Bicyclo[3.3.1]nonan-1-amine hydrochloride
(12b). Yield 83%, white crystals, mp >300°C [52].
Diamantan-1-amine hydrochloride (12c). Yield
84%, white crystals, mp 262–265°C [45].
This study was performed under financial support
by the Russian Science Foundation (project no. 15-
13-00084).
cis/trans-2,6-Dimethyladamantan-1-amine hy-
drochlorides (7a/7b). Yield 78% (mixture of isomers),
white crystals, mp >300°C. IR spectrum, ν, cm–1:
1
3300, 1610, 1500, 1120. H NMR spectrum, δ, ppm:
REFERENCES
3
3
0.72 d (3H, CH3, J = 7.6 Hz), 0.93 d (3H, CH3, J =
7.8 Hz), 1.36‒2.20 m (13H, CH, CH2, Ad), 8.47 br.s
(3H, NH3+). 13C NMR spectrum, δC, ppm: 13.89, 14.45,
19.31, 19.95, 23.37, 27.90, 31.42, 35.28, 35.72, 36.19,
38.46, 39.81, 43.09, 44.32, 57.56, 57.96. Mass spec-
trum, m/z (Irel, %): cis isomer 7a: 179 (10), 164 (2),
122 (4), 108 (100), 93 (5), 77 (2), 55 (4); trans isomer
7b: 179 (11), 164 (1), 122 (5), 108 (100), 93 (8), 71
(12), 57 (5). Found, %: C 66.89; H 10.32; N 6.57.
C12H22ClN. Calculated, %: C 66.80; H 10.28; N 6.49.
M 215.76.
1. Liu, J., Obando, D., Liao, V., Lifa, T., and Codd, R., Eur.
J. Med. Chem., 2011, vol. 46, p. 1949.
2. Cates, L.A., Gallio, R.L., and Cramer, M.B., J. Pharm.
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5. Brown, F. and Redfern, P.H., Br. J. Pharmacol., 1976,
vol. 58, p. 561.
6. Stoof, J.C., Booij, J., Drukarch, B., and Wolters, E.C.,
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cis/trans-3,6-Dimethyladamantan-1-amine hy-
drochlorides (9a/9b) and cis/trans-2,5-dimethylada-
mantan-1-amine hydrochlorides (10a/10b). Yield
90% (mixture of isomers). The mixture was separated
by fractional crystallization from 17% aqueous HCl.
cis/trans-3,6-Dimethyladamantan-1-amine
hydrochlorides (9a/9b). Yield 19%, white crystals,
9. Joubert, J., Geldenhuys, W.J., Van der Schyf, C.J.,
Oliver, D.W., Kruger, H.G., Govender, T., and
Malan, S.F., Chem.Med.Chem., 2012, vol. 7, no. 3,
p. 375.
10. Spasov, A.A., Khamidova, T.V., Bugaeva, L.I., and Mo-
rozov, I.S., Pharm. Chem. J., 2000, vol. 34, no. 1, p. 1.
11. Wanka, L., Iqbal, K., and Schreiner, P.R., Chem. Rev.,
1
mp >300°C. H NMR spectrum, δ, ppm: 0.72 d (3H,
3
CH3, J = 7.3 Hz), 0.93 s (3H, CH3), 1.13‒2.15 m
(13H, CH, CH2, Ad), 8.43 br.s (3H, NH3+). 13C NMR
spectrum, δC, ppm: 18.35, 18.67, 26.21, 26.78, 29.23,
29.68, 31.56, 33.71, 34.43, 34.81, 39.79, 42.65, 46.30,
52.06, 52.68. Mass spectrum, m/z (Irel, %): 179 (23),
164 (6), 122 (92), 108 (100), 93 (10), 77 (4), 55 (6).
Found, %: C 66.92; H 10.21; N 6.59. C12H22ClN.
Calculated, %: C 66.80; H 10.28; N 6.49. M 215.76.
2013, vol. 113, p. 3516.
12. Duque, M.D., Torres, E., Valverde, E., Barniol, M.,
Guardiola, S., Rey, M., and Vázquez, S., Recent
Advances in Pharmaceutical Sciences, Muñoz-
Torrero, D., Ed., Trivandrum, Kerala, India: Transworld
Research Network, 2011, p. 35.
cis-2,5-Dimethyladamantan-1-amine hydro-
chloride (10a). Yield 12%, white crystals, mp >300°C.
13. Klimochkin, Yu.N., Shiryaev, V.A., and Leonova, M.V.,
3
1H NMR spectrum, δ, ppm: 0.91 d (3H, CH3, J =
Izv. Akad. Nauk, Ser. Khim., 2015, p. 1473.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 12 2015