1772
KHUSNUTDINOV et al.
The structure of N-(3,5-dimethyladamant-1-yl)acyl-
amides II–V was confirmed by the IR and NMR spec-
troscopy methods.
GC-2014 [column 2 m × 3 mm, stationary phase
Silicone SE-30 (5%) supported on Chromaton N-AW-
HMDS, ramp from 50 to 270°C at a heating rate of
8 deg/min, carrier gas helium (47 mL/min)].
General procedure for the synthesis of N-(3,5-
dimethyladamant-1-yl)acetamides. The stainless steel
pressure microreactor (V = 17 mL) or glass vial was
charged under argon with 0.3 mmol of manganese-
containing catalyst, 10 mmol of 1-bromo-3,5-di-
methyladamantane I, and 30 mmol of amide. The reac-
tion mixture was heated at 120–130°C for 3–4 h with
stirring. After the reaction completed, the rector (vial)
was cooled to room temperature and opened. The
reaction mixture was washed with water, and then the
reaction product was extracted with methylene
chloride (3 × 5 mL). The solvent was removed under a
reduced pressure, and the residue was recrystallized.
N-(3,5-Dimethyladamant-1-yl)amides II–V were puri-
fied by column chromatography (silica gel, eluent –
hexane–ethyl acetate).
The IR spectra were recorded on a Bruker-Vertex
70V spectrometer from KBr pellets or slurry in mineral
oil. 13C NMR spectra were registered in CDCl3 on a
Bruker Avance-400 spectrometer operating at
100.62 MHz. Elemental analysis was performed on a
Carlo Erba 1106 analyzer.
ACKNOWLEDGMENTS
This work was financially supported by the Russian
Foundation for Basic Research (grant no. 14-03-
97029r_povolzhye-a) and the President of the Russian
Federation in the frame of support for young scientists
and graduate students engaged in advanced research
and development in priority areas of modernization of
the Russian economy (SP-4810.2013.4 ) for the 2013–
2015 years.
N-(3,5-Dimethyladamantan-1-yl)formamide (II).
Yield 78%, mp 69–70°C (hexane). Physico-chemical
constants and NMR spectral data correspond to the
literature data [7].
REFERENCES
N-(3,5-Dimethyladamantan-1-yl)acetamide (III).
Yield 99%, mp 109.5–110°C (hexane). Physico-
chemical constants and NMR spectral data correspond
to the literature data [11].
1. Bagrii, E.I., Adamantany: poluchenie, svoistva,
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1995, no. 293, p. 267.
N-(3,5-Dimethyladamant-1-yl)propanamide (IV).
Yield 98%, mp 102–103°C (ethanol). IR spectrum, ν,
cm–1: 1550 (NH), 1650 (C=O), 3300 (NH). 13С NMR
spectrum, δC, ppm: 22.32 (CH3), 29.07 (С3,5), 29.46
(С7), 29.97 (СН3), 31.48 (СН2), 41.59 (С6,9), 42.66
(С8), 44.68 (С2,10), 49.54 (С4), 51.73 (С1), 172.21
(C=O). Found, %: С 76.49; Н 10.68; N 5.89.
С15Н25NО. Calculated, %: С 76.55; Н 10.71; N 5.95. М
235.36.
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Nature, 1991, no. 34, p. 414. DOI: 10.1038/349414a0.
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N-(3,5-Dimethyladamant-1-yl)benzamide
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7. Wanka, L., Cabrele, C., Vanejews, M., and Schreiner, P.R.,
Eur. J. Chem., 2007, p. 1474. DOI: 10.1002/
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Yield 97%, sublimation point 80°C (10 mmHg). IR
spectrum, ν, cm–1: 1515 (amide II), 1580 (C=C,
arom.), 1650 (C=O), 1655 (amide I), 3440 (NH). 13С
NMR spectrum, δC, ppm: 29.82 (С7), 30.09 (C3,5),
30.19 (СН3), 40.37 (С6,9), 42.68 (С8), 45.15 (С2,10),
47.61 (С4), 50.62 (С1), 126.72, 128.67, 131.06, 135.92
(arom.), 166.78 (C=O). Found, %: С 80.48; Н 8.85; N
4.92. С19Н25NО. Calculated, %: С 80.52; Н 8.89; N
4.94.
8. Polis, Ya.Yu., Author’s Cerificate no. 1609406, 1977;
Ref. Zh. Khim., 1977, 20О46P.
9. Paulshock, M. and Watts, J.C., US Patent 3310469,
1967.
10. Khusnutdinov, R.I., Shchadneva, N.A., and Khisamo-
va, L.F., Russ. J. Org. Chem., 2015, vol. 51, no. 4,
p. 476. DOI: 10.1134/S107042801504003X.
The reaction progress was monitored by gas-liquid
chromatography on a Shimadzu GC-9A instrument,
11. Plakhotnik, V.M., Kovtun, V.Yu., and Yashunskii, V.G.,
Zh. Org. Khim., 1982, vol. 18, p. 1001.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 7 2015