LETTER
One-Pot Synthesis of Cationic Amphiphiles
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availability when compared to natural terpenols. The
results of DNA transfection will be communicated else-
where in due course.
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Supporting Information for this article is available online at
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Acknowledgment
The authors are thankful to Dr. T. K. Chakraborty, Director, CDRI
for support for the synthesis of bioactive compounds and the SAIF
Division of CDRI for spectral data and DST and CSIR, New Delhi
for financial support. We also thank Shilah, University of Portland,
USA for reading the manuscript. This is CDRI’s communication
number 8059.
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References and Notes
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(39) Representative Procedure for the Preparation of N,N,N-
Triethyltridecan-1-aminium Chloride (2a)
A solution of 1a (5.0 g, 25.0 mmol) in CH2Cl2 (10 mL) and
Et3N (10 mL) was added dropwise to a stirred solution of
POCl3 (7.6 g, 50.0 mmol) in dichloromethane (10 mL) at 0
°C. After stirring the solution for 1 h, a solution of N,N-
diethylethanolamine (4.4 g, 37.5 mmol) in Et3N (10 mL) was
added. The whole reaction mixture was stirred for 1 h at 0 °C
followed by 2 h at r.t. Water (5 mL) was added dropwise to
the reaction mixture and stirred for additional 30 min. Then,
10 mL of 10% solution of citric acid and MeOH–H2O (1:1)
was added to the reaction mixture and extracted into CHCl3
(3 × 100 mL). The combined organic layer was washed with
MeOH–H2O (1:1) and dried over anhyd Na2SO4. The
solvent was evaporated under reduced pressure, and the
crude product was chromatographed on silica gel as
stationary phase and CHCl3–MeOH–H2O (91.5:8:0.5) as
mobile phase to afford the compound 2a (4.26 g, 60%). 1H
NMR (300 MHz, CDCl3): d = 3.60–3.03 (m, 8 H), 1.43 (m,
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2 H), 1.18–1.04 (m, 29 H), 0.70 (t, J = 6.2 Hz, 3 H). 13
C
NMR (50 MHz, CDCl3): d = 57.6, 53.6 (3 C), 32.2, 30.0 (6
C), 29.8, 29.7, 29.5, 26.8, 26.1, 23.0, 22.2, 14.4. ESI-MS:
m/z = 284.4.
(40) Representative Procedure for the Preparation of 1-
Nonylpyridinium Chloride (2f)
A solution of 1f (5 g, 26.9 mmol) in CH2Cl2 (10 mL) and
pyridine (10 mL) was added dropwise to the stirred solution
of POCl3 (8.25 g, 53.7 mmol) in CH2Cl2 (10 mL) at 0 °C.
After stirring for 1 h, a solution of N,N-diethylethanolamine
(4.7 g, 40.3 mmol) in pyridine (10 mL) was then added at 0
°C. The whole reaction mixture was stirred for 1 h at 0 °C
followed by 2 h at r.t. Water (5 mL) was added dropwise to
the reaction mixture and stirred for additional 30 min. Then,
10 mL of 10% solution of citric acid and MeOH–H2O (1:1)
was added in the reaction mixture and extracted into CHCl3
(2 × 100 mL). The combined organic layer was washed with
MeOH–H2O (1:1) and dried over anhyd Na2SO4. The
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Synlett 2011, No. 12, 1687–1692 © Thieme Stuttgart · New York