D
M. Obst et al.
Letter
Synlett
References and Notes
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(24) General Procedure for the Synthesis of Propargyl Amines
The aldehyde was added to the DES (for preparation of DES, see
the Supporting Information), followed by the amine (1.5 equiv)
and the alkyne (1.5 equiv), and the reaction was performed at
80 °C for 20 h. For workup, the hot reaction mixture was diluted
with 2 mL water and extracted four times with 5 mL EtOAc. The
combined organic layers were dried over Na2SO4, and the
product was isolated applying flash column chromatography
(gradient of EtOAC in PE).
4-[1-(4-Iodophenyl)-3-phenyl-2-propyn-1-yl]-morpholine
(5)
(12) Gore, S.; Baskaran, S.; König, B. Green Chem. 2011, 13, 1009.
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2014, 6, 2854.
4-Iodobenzaldehyde (232 mg, 1.0 mmol) was reacted with mor-
pholine (131 μL, 1.5 mmol) and phenylacetylene (165 μL, 1.5
mmol). The reaction was performed in 1 g of melt, prepared
from 0.31 g ZnCl2 and 0.69 g DMU; yield 336 mg (82%). 1H NMR
(300 MHz, CDCl3): δ = 7.73–7.69 (m, 2 H), 7.57–7.51 (m, 2 H),
7.43–7.40 (m, 2 H), 7.37–7.32 (m, 3 H), 4.74 (s, 1 H), 3.80–3.68
(m, 4 H), 2.63 (t, J = 4.5 Hz, 4 H). 13C NMR (75 MHz, CDCl3): δ =
137.8, 137.4, 131.9, 130.6, 128.5, 128.4, 122.7, 93.6, 89.0, 84.3,
67.1, 61.4, 49.9. ESI-MS: m/z calcd for
404.0512; found: 404.0533. EA (%, theoretical values in brack-
ets): C, 56.50 (56.59); H, 4.36 (4.50); N, 3.38 (3.47).
C
19H18INO [MH]+:
(18) Patil, U. B.; Singh, A. S.; Nagarkar, J. M. RSC Adv. 2014, 4, 1102.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–D