S. Khaksar et al. / Journal of Fluorine Chemistry 131 (2010) 106–110
109
Scheme 2. The reaction of 2,3-epoxyallyl phenyl ether and aniline in different solvents.
we examined the reaction of 2,3-epoxyallyl phenyl ether and
aniline in different solvents. The results are summarized in
Scheme 2, and show that, high conversions were obtained with
TFE and HFIP. Although there is no solid evidence to support the
catalytic mechanism of TFE in the reaction, it is surely
reasonable to propose that the high polarity and the hydrogen
bonding interaction of TFE with epoxides may be responsible for
the promotion of the reaction.
1-Phenoxy-3-piperazin-1-yl-propan-2-ol (3ag): 1H NMR (CDCl3,
500 MHz): 1.44–1.62 (m, 6H), 2.37–2.61 (m, 6H), 3.95–4.09 (m,
3H), 6.92–6.96 (m, 2H), 7.26–7.29 (m, 3H) 13C NMR (CDCl3,
125 MHz): 24.2, 26.1, 54.7, 61.2, 65.3, 70.4, 76.8, 114.6, 120.8,
d
d
129.4, 129.6, 158.8.
2-Phenyl-2-phenylamino-ethanol (3da): 1H NMR (CDCl3,
500 MHz):
d 3.78 (dd, 1H, J = 5.0, 10.5 Hz), 3.90 (dd, 1H, J = 4.0,
10.5 Hz), 4.55 (dd, 1H, J = 6.5, 10.8 Hz), 6.40 (d, 2H, J = 7.5 Hz), 6.80
(t, 1H, J = 7.8 Hz), 6.95 (d, 2H, J = 8.0 Hz), 7.30–7.45 (m, 5H). 13C
3. Conclusions
NMR (CDCl3, 125 MHz):
128.5, 129.7, 136.1, 146.8.
1-Allyloxy-3-morpholin-4-yl-propan-2-ol (3cd): 1H NMR (CDCl3,
500 MHz): 2.1–2.3 (m, 6H), 3.2 (dd, 2H, J = 4.5, 11.2 Hz), 3.45–4.1
(m, 8H), 4.9–5.1 (m, 2H), 5.6–5.7 (m, 1H). 13C NMR (CDCl3,
125 MHz): 53.6, 61.2, 66.2, 66.5, 72.5, 116.6, 134.4.
1-Allyloxy-3-(4-chloro-phenylamino)-propan-2-ol (3cc): 1H NMR
(CDCl3, 500 MHz): 3.1–3.5 (m, 5H), 4.0–4.1 (m, 3H), 5.23 (dd, 2H,
d 57.8, 68.5, 112.1, 117.8, 126.4, 127.43,
In summary, we have described herein an efficient methodol-
ogy for the synthesis of
b
-amino alcohols using several epoxides
d
and amines in good to excellent isolated yields. In contrast to the
existing methods using potentially hazardous catalysts/additives,
the present method offers the following competitive advantages:
(i) avoiding the use of any base, metal or Lewis acid catalyst, (ii)
short reaction time, (iii) ease of product isolation/purification by
non-aqueous work-up, (iv) high regioselectivity, (v) no side
reaction, and (vi) low costs and simplicity in process and handling.
The recovered TFE can be reusable.
d
d
J = 5, 18 Hz, 2H), 5.91–5.94 (m, 1H), 6.5 (d, 2H, J = 8 Hz), 7.1 (d, 2H,
J = 8 Hz). 13C NMR (CDCl3, 125 MHz):
d 46.7, 68.8, 72.3, 72.4, 114.2,
117.6, 122.3, 129.1, 134.3, 146.8.
1-Morpholin-4-yl-butan-2-ol (3bd): 1H NMR (CDCl3, 500 MHz):
0.76 (t, 3H, J = 7.4 Hz), 1.21–1.26 (m, 2H), 2.04–2.18 (m, 7H), 3.4–
d
4. Experimental
3.5 (m, 5H). 13C NMR (CDCl3, 125 MHz):
d 9.62, 27.5, 46.1, 53.6,
64.4, 66.7, 67.2, 67.8.
General procedure: To a solution containing epoxide (1 mmol),
in TFE (2 mL) was added to the amine (1 mmol) and the mixture
was vigorously stirred at r.t. for 6 h. The products were isolated
after selective evaporation of TFE and were purified by silica gel
column chromatography eluted by AcOEt and hexane (1:1) to
Acknowledgement
Research supported by the National Research Council of I.R. Iran
as a National Research project under the number 984.
afford the corresponding pure
b-amino alcohols in very good
References
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Spectroscopic data for selected examples are shown below.
1-Phenoxy-3-phenylamino-propan-2-ol (3aa): 1H NMR (CDCl3,
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d 3.22–3.26 (m, 1H), 3.38–3.42 (m, 1H), 3.60–3.65 (m,
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d
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