1
118
K. Rajeswari, K. Pandiarajan / Spectrochimica Acta Part A 78 (2011) 1110–1118
4.2.3. 3,5-Bis[(E)-thienylmethylene]-2r,6c-diphenylpiperidin-4-
Acknowledgement
one (3a)
To a solution of 3 (0.01 mol) prepared by following the procedure
of Baliah et al. [15] in ethanol (20 mL) thiophene-2-carboxaldehyde
0.02 mol) and sodium hydroxide solution (20%, 20 mL) were added.
The authors are thankful to SAIF, IIT Chennai for recording NMR
and mass spectra.
(
The mixture was warmed on a water bath for 20 min. The solid sep-
arated on cooling was filtered and recrystallized from 95% ethanol.
Yield 75%; mp 260 C.
Appendix A. Supplementary data
◦
Supplementary data associated with this article can be found, in
the online version, at doi:10.1016/j.saa.2010.12.062.
4.3. Methods
References
The melting points were determined in open capillaries and are
uncorrected. IR spectra were recorded on an AVATAR 330 FT-IR
Thermo Nicolet spectrometer in KBr pellets. Mass spectra were
recorded on JEOL GCmate mass spectrometer.
[
1] J.R. Dimmock, P. Kumar, A.J. Nazarali, N.L. Motaganahalli, T.P. Kowalchut, M.A.
Beaszely, J.W. Quail, E.O. Oloo, T.M. Allen, J. Szydlowski, E. Declercq, J. Balzarini,
Eur. J. Med. Chem. 35 (2000) 967–977.
1
H NMR spectra were recorded for 1a–c, 2a, 2c, 3a and 2, on a
[2] H.N. Pati, U. Das, J.W. Quail, M. Kawase, H. Sakagami, J.R. Dimmock, Eur. J. Med.
Chem. 43 (2008) 1–7.
[
Bruker AMX-400 spectrometer operating at 399.88 MHz and for 2b,
on a Bruker DRX-500 NMR spectrometer operating at 500.13 MHz.
The spectral parameters are as follows: acquisition time = 1.5–2.0 s,
number of scans = 16, number of data points = 32 K and spectral
width = around 10,000 Hz.
3] H.N. Pati, U. Das, S. Das, B. Bandy, E. De Clercq, J. Balzarini, M. Kawase, H.
Sakagami, J.W. Quail, J.P. Stables, J.R. Dimmock, Eur. J. Med. Chem. 44 (2009)
54–62.
4] J.R. Dimmock, A. Jha, G.A. Zello, J.W. Quail, E.O. Oloo, K.T.H. Nienaber, E.S. Kowal-
czyk, T.M. Allen, C.L. Santos, E. De Clercq, J. Balzarini, E.K. Manavathu, J.P. Stables,
Eur. J. Med. Chem. 37 (2002) 961–972.
[
Proton decoupled 13C NMR spectra were recorded for 1a–c,
[5] H.I. El-Subbagh, S.M. Abu-Zaid, M.A. Mahran, F.A. Badria, A.M. Al-Obaid, J. Med.
Chem. 43 (2000) 2915–2921.
[
2
a, 2c, 3a and 2, on a Bruker AMX-400 spectrometer operating at
6] P. Tongwa, T.L. Kinibrugh, R. Geetha, V.N. Kicchaiahgari, T.V. Khrustalev, Timo-
feeva, Acta Crystallogr. C 65 (2009) 155–159.
1
00.6 MHz and for 2b, on a Bruker DRX-500 NMR spectrometer
operating at 125.77 MHz. The spectral parameters are as follows:
acquisition time = 0.5–1.2 s, number of scans = 1000, number of data
points = 32 K and spectral width = around 30,000 Hz.
[7] K. Rajeswari, K. Pandiarajan, P. Gayathri, A. Thiruvalluvar, Acta Crystallogr. E
5 (2009) 885.
8] D.N. Kevill, E.D. Weiler, N.H. Cromwell, J. Org. Chem. 29 (1964) 1276–
278.
pounds, sixth ed., Wiley, New York, 1998, p. 229.
6
[
1
1
1
H– H COSY spectrum of 2b was recorded on a Bruker AMX-
4
2
00 spectrometer, using standard parameters. HSQC spectra of 1a,
b, 3a and 3, HMBC spectra of 1a, 1b, 2b, 3a and 2, and phase-
[
10] R.M. Silverstein, F.X. Webster, Spectrometric Identification of Organic Com-
pounds, sixth ed., Wiley, New York, 1998, p. 232.
sensitive NOESY spectrum of 2b were recorded on a Bruker DRX-
00 NMR spectrometer using standard parameters. The number
of data points was 1 K. For NOESY spectrum the mixing time was
00 ms.
All NMR measurements were made in 5 mm NMR tubes using
[11] R.M. Silverstein, F.X. Webster, Spectrometric Identification of Organic Com-
pounds, sixth ed., Wiley, New York, 1998, p. 209.
5
[
[
13] K. Ramalingam, K.D. Berlin, N. Satyamurthy, R. Sivakumar, J. Org. Chem. 44
8
(
1979) 471–478.
[14] S.R. Salman, Org. Magn. Reson. 20 (3) (1982) 151–153.
15] V. Baliah, A. Ekambaram, T.S. Govindarajan, Curr. Sci. 23 (1954)
64.
[
solutions made by dissolving about 10 mg of the material in 0.5 mL
of CDCl3.
2