E
L.-y. Li et al.
Letter
Synlett
Funding Information
(10) (a) Xie, L.; Wu, Y.; Yi, W.; Zhu, L.; Xiang, J.; He, W. J. Org. Chem.
2013, 78, 9190. (b) Tanemura, K.; Suzuki, T.; Nishida, Y.;
Satsumabayashi, K.; Horaguchi, T. Chem. Commun. 2004, 470.
(c) Perrine, D. M.; Ross, J. T.; Nervi, S. J.; Zimmerman, R. H.;
Short, A. J. Chem. Ed. 2000, 77, 1479. (d) Jiang, Q.; Sheng, W.;
Guo, C. Green Chem. 2013, 15, 2175. (e) Arbuj, S. S.; Waghmode,
S. B.; Ramaswamy, A. V. Tetrahedron Lett. 2007, 48, 1411.
(11) Evans, R. W.; Zbieg, J. R.; Zhu, S.; Li, W.; MacMillan, D. W. J. Am.
Chem. Soc. 2013, 135, 16074.
This work was supported financially by the Natural Science Founda-
tion of Sichuan province, China (2017JY0055) and the Youth Innova-
tion Promotion Association CAS (2018402).
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Supporting Information
Supporting information for this article is available online at
(12) Jiang, Q.; Xu, B.; Zhao, A.; Jia, J.; Liu, T.; Guo, C. J. Org. Chem.
2014, 79, 8750.
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(13) Guha, S.; Rajeshkumar, V.; Kotha, S. S.; Sekar, G. Org. Lett. 2015,
17, 406.
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Chem. 2014, 7451. (c) Sahoo, S. C.; Nath, U.; Pan, S. C. Eur. J. Org.
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References and Notes
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(15) Preparation of 2-[Methyl(phenyl)amino]-1-phenylethan-1-
one (3j) – General Procedure
2-Hydroxyacetophenone (0.1 mmol) and morpholine (0.1
mmol) were added in a reaction vessel followed by catalytic
PTSA (0.005 mmol). The reaction mixture was stirred under
nitrogen atmosphere overnight at 50 ℃. After full conversion of
the starting material, the reaction mixture was cooled down to
room temperature and purified by silica gel flash column
directly (eluent: petroleum ether/ethyl acetate = 3:1); colorless
oil, 14.2 mg (63%). 1H NMR (400 MHz, CDCl3): δ = 8.11–7.96 (m,
2 H), 7.64 (t, J = 7.4 Hz, 1 H), 7.52 (t, J = 7.6 Hz, 2 H), 7.24 (dd, J =
8.7, 7.4 Hz, 2 H), 6.83–6.59 (m, 3 H), 4.81 (s, 2 H), 3.13 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 196.48 (s), 149.20 (s), 135.46 (s),
133.55 (s), 129.21 (s), 128.82 (s), 127.81 (s), 117.12 (s), 112.28
(s), 77.34 (s), 77.03 (s), 76.71 (s), 58.99 (s), 39.58 (s). HRMS
(ESI): C15H15NO neutral mass: 225.11536; observed [M + H]+:
226.12296.
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1996, 37, 2939. (d) Miyairi, S.; Maeda, K.; Oe, T.; Kato, T.;
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R.; Caboni, P.; Secci, F.; Aitken, D. J.; Frongia, A. Eur. J. Org. Chem.
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Chem. Commun. 2013, 49, 8812. (e) Frongia, A.; Melis, N.; Serra,
I.; Secci, F.; Piras, P. P.; Caboni, P. Asian J. Org. Chem. 2014, 3,
378. (f) Aitken, D. J.; Caboni, P.; Eijsberg, H.; Frongia, A.; Guillot,
R.; Ollivier, J.; Piras, P. P.; Secci, F. Adv. Synth. Catal. 2014, 356,
941.
(16) Preparation of 2-(Indolin-1-yl)-1-phenylpropan-1-one (4i)
The reaction executed with general procedure, 24 h at 80 °C;
brown oil, 11.3 mg (45%). 1H NMR (400 MHz, CDCl3): δ = 8.12–
8.04 (m, 2 H), 7.64–7.53 (m, 1 H), 7.53–7.39 (m, 2 H), 7.19–7.07
(m, 2 H), 6.70 (dd, J = 10.7, 3.9 Hz, 1 H), 6.58 (d, J = 7.7 Hz, 1 H),
5.22–5.10 (m, 1 H), 3.47 (dd, J = 18.2, 9.5 Hz, 1 H), 3.32 (td, J =
8.9, 5.2 Hz, 1 H), 3.01–2.85 (m, 2 H), 1.40 (t, J = 7.4 Hz, 3 H). 13
C
NMR (101 MHz, CDCl3): δ = 199.23 (s), 150.03 (s), 135.78 (s),
133.24 (s), 130.16 (s), 128.54 (s), 127.38 (s), 124.71 (s), 117.80
(s), 106.31 (s), 55.04 (s), 47.65 (s), 28.26 (s), 10.15 (s). HRMS
(ESI): C17H17NO2 neutral mass: 251.13101; observed [M + H]+:
252.13811.
(7) Li, G.; Tang, L.; Liu, H.; Wang, Y.; Zhao, G.; Tang, Z. Org. Lett.
2016, 18, 4526.
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Decker, A. M.; Page, K. M.; Rothman, R. B. ACS Med. Chem. Lett.
2014, 5, 623. (b) Aarde, S. M.; Huang, P. K.; Creehan, K. M.;
Dickerson, T. J.; Taffe, M. A. Neuropharmacology 2013, 71, 130.
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Vandewater, S. A.; Creehan, K. M.; Houseknecht, K. L.; Dickerson,
T. J.; Taffe, M. A. Addict. Biol. 2013, 18, 786.
(9) (a) Myers, M. C. W.; Iera, J. A.; Bang, J.-K.; Hara, T.; Saito, S. i.;
Zambetti, G. P.; Appella, D. H. J. Am. Chem. Soc. 2005, 127, 6152.
(b) Meltzer, P. C.; Butler, D.; Deschamps, J. R.; Madras, B. K.
J. Med. Chem. 2006, 49, 1420. (c) Carroll, F. I.; Blough, B. E.;
Abraham, P.; Mills, A. C.; Holleman, J. A.; Wolckenhauer, S. A.;
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Gatch, M. B.; Forster, M. J. J. Med. Chem. 2009, 52, 6768.
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(17) Preparation of 1-(4-Bromophenyl)-2-morpholinobutan-1-
one (4n)
The reaction executed with the general procedure; yellow oil,
17.1 mg (55%). 1H NMR (400 MHz, CDCl3): δ = 8.07–7.86 (m, 2
H), 7.75–7.56 (m, 2 H), 3.81 (dd, J = 9.3, 4.7 Hz, 1 H), 3.68 (dd, J =
10.8, 6.2 Hz, 4 H), 2.75–2.63 (m, 2 H), 2.62–2.48 (m, 2 H), 1.97–
1.70 (m, 2 H), 0.92–0.84 (m, 4 H). 13C NMR (101 MHz, CDCl3):
δ = 198.59 (s), 131.82 (s), 130.21 (s), 77.33 (s), 77.02 (s), 76.70
(s), 70.99 (s), 67.31 (s), 50.28 (s), 19.06 (s), 10.97 (s), 1.02 (s).
HRMS (ESI): C14H18BrNO2 neutral mass: 311.05209; observed
[M + H]+: 312.05453.
(18) Sánchez-Viesca, F. Am. J. Chem. 2015, 5, 86.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2019, 30, A–E