SYNTHESIS AND STRUCTURE
2059
Scheme 2.
H2
C
14
H
toluene
15
+
C60 CH3NHCH2COOH +
R
C
18
CH3
t, 4 h
N
O
17
13CH
I, II
6 (IV).
16
9
2
1
2
4
1
5
8
7
10
11
III, IV
3
N
3
(III),
O
6
R=
N
12
5
4
R
benzaldehyde I and 9.8 mg (0.278 mmol) of N-me- (С16), 69.78 (С15), 68.71 (С14), 50.10 (С4), 49.90 (С2),
thylglycine. The mixture was refluxed for 4 h. After 40.80 (С13), 39.78 (С18), 39.60 (С5), 24.19 (С6). Mass
the reaction was completed, the reaction mixture was spectrum, m/z 935.150 [М – Н]+. М 936.96.
chromatographed on silica gel. Yield 23 mg (88%). 1Н
Commercial fullerene C60 of 99.5% purity was used.
NMR spectrum (400.13 MHz, CDCl3), δ, ppm, (J, Hz):
1H and 13C NMR spectra were recorded on a Bruker
Avance-400 spectrometer in a СDСl3–СS2 solution
(1 : 5), internal reference TMS. Mass spectra were
registered on a MALDI TOF/TOF Autoflex-III Bruker
spectrometer.
2.82 s (3Н, Н18), 3.19 t (2Н, Н2, J1,2 4.8), 3.37 t (2Н,
Н4, J4,5 4.8), 3.86 m (4Н, Н1, Н5), 4.27 d (1Н, Н15b
,
J15a,15b 9.2), 4.89 s (1Н, Н16), 4.99 d (1Н, Н15a, J15a,15b
9.2), 6.92 m (2Н, Н7, Н11), 7.68 d (1Н, Н10, J10,11 6.4),
7.76 d (1Н, Н8, J7,8 8.8). 13С NMR spectrum
(100.62 MHz, CDCl3), δС, ppm; 135.53–156.09 (58С,
С19–С76), 154.71 (С12), 131.43 (С10), 129.96 (С8),
127.77 (С9), 115.18 (С11), 113.34 (С7), 83.03 (С16),
69.77 (С15), 68.66 (С14), 66.22 (С5), 66.29 (С4), 48.79
(С2), 47.32 (С4), 39.79 (С18), 29.83 (С13).
REFERENCES
1. Fullereny (Fullerenes), Sidorov, L.N., Yurovskaya, M.A.,
Borshchevskii, A.Ya., Trushkov, I.V., and Ioffe, I.N.,
Eds., Moscow: Ekzamen, 2005.
N-Methyl-1-(4-piperidylphenyl)fullero-C60[1.9]-
pyrrolidine (IV) was obtained similarly from 40 mg
(0.0555 mmol) of С60, 5.2 mg (0.0275 mmol) of 4-
piperidylbenzaldehyde II, and 9.8 mg (0.278 mmol) of
N-methylglycine in 40 mL of toluene. Yield 16 mg
2. Yurovskaya, M.A. and Trushkov, I.V., Russ. Chem.
Bull., 2002, no. 3, p. 367.
3. Jinying Zhang, Porfyrakis, K., Morton, J.J.L., Sam-
brook, M.R., Harmer, J., Li Xiao, Ardavan, A., and
Briggs, G.A.D., J. Phys. Chem. (C), 2008, vol. 112,
no. 8, p. 2003. DOI: 10.1021/jp711861z.
4. Bosi, S., Da Ros, T., Spalluto, G., Balzarini, J., and
Prato, M., Bioorg. Med. Chem. Lett., 2003, vol. 13,
p. 4437. DOI: 10.1016/j.bmcl.2003.09.016.
5. Nurkenov, O.A., Fazylov, S.D., Arinova, A.E., Tur-
dybekov, K.M., Turdybekov, D.M., Talypov, S.A., and
Ibragimov, B.T., Russ. J. Gen. Chem., 2013, vol. 84,
no. 10, p. 1864. DOI: 10.1134/S1070363213100113.
1
(62%). Н NMR spectrum (400.13 MHz, CDCl3), δ,
ppm, (J, Hz): 1.75 br.s (6Н, Н1, Н5, Н6), 2.81 s (3Н,
Н18), 3.21 m (2Н, Н2, Н4), 4.26 d (1Н, Н15b, J15a,15b
9.2), 4.88 s (1Н, Н16), 4.99 d (1Н, Н15a, J15a,15b 9.2),
6.98 br.s (2Н, Н7, Н11), 7.65 br.s (1Н, Н8, Н10). 13С
NMR spectrum (100.62 MHz, CDCl3), δС, ppm;
135.48–156.18 (58С, С19–С76), 153.89 (С12), 129.90
(С10), 129.60 (С8), 116.00 (С11), 115.70 (С7), 83.11
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 10 2014