Dingyi Yu and Yugen Zhang
FULL PAPERS
tory spectroscopic data. New compounds were characterized
with NMR, HR-MS and elemental analysis.
(CHO), 135.19, 132.21, 129.66, 129.49, 89.13, 84.27, 47.36,
41.88, 12.60. GC-MS: m/z=215.
N,N-Diethyl-3-phenylprop-2-yn-1-amine (1b): 1H NMR
(400 MHz, CDCl3): d=7.41–7.44 (m, 2H, Ar-H), 7.28–7.30
(m, 3H, Ar-H), 3.64 (s, 2H, CH2), 2.62 (q, J=7.2 Hz, 4H,
CH2), 1.12 (t, J=7.2 Hz, 6H, CH3); 13C NMR (100 MHz,
CDCl3): d=131.65, 128.19, 127.86, 123.30, 84.90, 84.31,
47.27, 41.36, 12.62; GC-MS: m/z=187.
{4-[3-(Diethylamino)prop-1-ynyl]phenyl}methanol
(9b):
1H NMR (400 MHz, CDCl3): d=7.38 (d, J=8.4 Hz, 2H, Ar-
H), 7.27 (d, J=8.4 Hz, 2H, Ar-H), 4.64 (s, 2H, CH2), 3.58 (s,
2H, CH2), 3.17 (br, s, 1H, OH), 2.59 (q, J=7.2 Hz, 4H,
CH2), 1.10 (t, J=7.2 Hz, 6H, CH3); 13C NMR (100 MHz,
CDCl3): d=141.11, 131.72, 126.59, 122.16, 84.94, 83.90,
64.44, 47.17, 41.20, 12.34; GC-MS: m/z=217; HR-MS (ESI):
m/z=217.1465, calcd. for C14H19NO (M+ÀO) 217.1467; ele-
mental analysis calcd. (%) for 9b [C14H19NO (217)]: C 77.38,
H 8.81, N 6.45; found: C 77.27, H 8.43, N 6.10.
N,N-Diethyl-3-p-tolylprop-2-yn-1-amine (2b): 1H NMR
(400 MHz, CDCl3): d=7.31 (d, J=8.0 Hz, 2H, Ar-H), 7.08
(d, J=7.6 Hz, 2H, Ar-H), 3.63 (s, 2H, CH2), 2.61 (q, J=
7.2 Hz, 4H, CH2), 2.33 (s, 3H, CH3), 1.11 (t, J=7.2 Hz, 6H,
CH3); 13C NMR (100 MHz, CDCl3): d=137.83, 131.49,
128.88, 120.18, 84.91, 83.45, 47.20, 41.34, 21.34, 12.58; GC-
MS: m/z=201.
3-Cyclohexenyl-N,N-diethylprop-2-yn-1-amine
(10b):
1H NMR (400 MHz, CDCl3): d=6.05 (m, 1H, CH), 3.52 (s,
2H, CH2), 2.55 (q, J=7.2 Hz, 4H, CH2), 2.05–2.12 (m, 4H,
CH2), 1.55–1.65 (m, 4H, CH2), 1.06 (t, J=7.2, 6H);
13C NMR (100 MHz, CDCl3): d=134.03, 120.56, 86.74,
81.13, 47.13, 41.23, 29.48, 15.51, 22.28, 21.48, 12.60. GC-MS:
m/z=191.
N,N-Diethyl-3-p-(4-biphenylprop)-2-yn-1-amine
(3b):
1H NMR (400 MHz, CDCl3): d=7.58 (d, J=6.8 Hz, 2H, Ar-
H), 7.50–7.56 (m, 4H, Ar-H), 7.45 (t, J=7.4 Hz, 2H, Ar-H),
7.36 (t, J=7.2 Hz, 1H, Ar-H), 3.68 (s, 2H, CH2), 2.65 (q, J=
7.2 Hz, 4H, CH2), 1.14 (t, J=7.2 Hz, 6H, CH3); 13C NMR
(100 MHz, CDCl3): d=140.61, 140.34, 132.07, 128.78, 127.51,
126.94, 126.87, 122.20, 85.01, 84.77, 47.28, 41.42, 12.62; GC-
MS: m/z=263; HR-MS (ESI): m/z=263.1667, calcd. for
C19H21N (M+ÀO): 263.1674; elemental analysis calcd. (%)
for 3b [C19H21N (263)]: C 86.65, H 8.04, N 5.32; found: C
86.74, H 7.98, N 5.15.
N,N-Diethyl-4,4-dimethylpent-2-yn-1-amine
(11b):
1H NMR (400 MHz, CDCl3): d=3.40 (s, 2H, CH2), 2.48 (q,
J=7.2 Hz, 4H, CH2), 1.18 (s, 9H, CH3), 1.03 (t, J=7.2 Hz,
6H, CH3); 13C NMR (100 MHz, CDCl3): d=93.65, 72.31,
46.91, 40.76, 31.22, 27.38, 12.46; GC-MS: m/z= 167.
1
N,N-Diethylhept-2-yn-1-amine (12b): H NMR (400 MHz,
CDCl3): d=3.32 (s, 2H, CH2), 2.47 (q, J=7.2 Hz, 4H, CH2),
2.13 (t, J=6.8 Hz, 2H, CH2), 1.32–1.44 (m, 4H, CH2), 1.00
(t, J=7.6 Hz, 6H, CH3), 0.85 (t, J=7.0 Hz, 3H, CH2);
13C NMR (100 MHz, CDCl3): d=84.80, 74.05, 46.95, 40.76,
30.96, 21.81, 18.25, 13.47, 12.43; GC-MS: m/z=167.
3-[3-(Diethylamino)prop-1-ynyl]phenol (4b): 1H NMR
(400 MHz, CDCl3): d=7.72 (br, s, 1H, OH), 7.12 (t, J=
8.0 Hz, 1H, Ar-H), 6.89–6.93 (m, 2H, Ar-H), 6.77 (m, 1H,
Ar-H), 3.64 (s, 2H, CH2), 2.70 (q, J=7.2 Hz, 4H, CH2), 1.13
(t, J=7.2 Hz, 6H, CH3); 13C NMR (100 MHz, CDCl3): d=
156.46, 129.48, 123.82, 123.31, 118.86, 116.31, 85.76, 82.83,
47.05, 41.18, 11.53. GC- MS: m/z=203; HR-MS (ESI):
m/z=203.1305, calcd. for C13H17NO (M+ÀO): 203.1310; ele-
mental analysis calcd. (%) for 4b [C13H17NO (203)]: C 76.81,
H 8.43, N 6.89; found: C 76.52, H 8.13, N 6.67.
N,N-Diisopropyl-3-phenylprop-2-yn-1-amine
(15b):
1H NMR (400 MHz, CDCl3): d=7.39–7.41 (m, 2H, Ar-H),
7.27–7.29 (m, 3H, Ar-H), 3.65 (s, 2H, CH2), 3.26 (m, 2H,
CH), 1.15 (d, J=6.8 Hz, 12H, CH3); 13C NMR (100 MHz,
CDCl3): d=131.40, 128.17, 127.69, 123.73, 88.92, 83.48,
48.43, 34.74, 20.62; GC-MS: m/z=215.
1-(3-Phenylprop-2-ynyl)pyrrolidine
(16b):
1H NMR
N,N-Diethyl-3-(4-methoxyphenyl)prop-2-yn-1-amine (5b):
1H NMR (400 MHz, CDCl3): d=7.33 (d, J=8.8 Hz, 2H, Ar-
H), 6.79 (d, J=9.2 Hz, 2H, Ar-H), 3.76 (s, 3H, OCH3), 3.60
(s, 2H, CH2), 2.59 (q, J=7.2 Hz, 4H, CH2), 1.09 (t, J=
7.2 Hz, 6H, CH3); 13C NMR (100 MHz, CDCl3): d=159.15,
132.94, 115.34, 113.68, 84.57, 82.59, 55.09, 47.14, 41.30, 12.51;
GC-MS: m/z=215.
(400 MHz, CDCl3): d=7.42–7.44 (m, 2H, Ar-H), 7.28–7.30
(m, 3H, Ar-H), 3.63 (s, 2H, CH2), 2.69 (t, J=6.8 Hz, 4H,
CH2), 1.84 (m, 4H, CH2); 13C NMR (100 MHz, CDCl3): d=
131.71, 128.22, 127.97, 123.23, 85.32, 84.37, 52.81, 44.09,
23.98; GC-MS: m/z=185.
4-(3-Phenylprop-2-ynyl)morpholine
(17b):
1H NMR
(400 MHz, CDCl3): d=7.41–7.44 (m, 2H, Ar-H), 7.27–7.29
(m, 3H, Ar-H), 3.76 (t, J=4.6 Hz, 4H, CH2), 3.49 (s, 2H,
CH2), 2.63 (t, J=4.6 Hz, 4H, CH2); 13C NMR (100 MHz,
CDCl3): d=131.60, 128.16, 128.08, 122.82, 85.45, 83.91,
66.77, 52.31, 47.95; GC-MS: m/z=201.
3-(4-Chlorophenyl)-N,N-diethylprop-2-yn-1-amine
(6b):
1H NMR (400 MHz, CDCl3): d=7.34 (d, J=8.4 Hz, 2H, Ar-
H), 7.26 (d, J=8.8 Hz, 2H, Ar-H), 3.63 (s, 2H, CH2), 2.61
(q, J=7.2 Hz, 4H, CH2), 1.11 (t, J=7.0 Hz, 6H, CH3);
13C NMR (100 MHz, CDCl3): d=133.81, 132.87, 128.48,
121.76, 85.46, 83.78, 47.26, 41.35, 12.57; GC-MS: m/z=221.
N,N-Diethyl-3-phenyl-2-deuteriopropyn-1-amine
(22b):
1H NMR (400 MHz, CDCl3): d=7.41–7.44 (m, 2H, Ar-H),
7.28–7.30 (m, 3H, Ar-H), 2.62 (q, J=7.2 Hz, 4H, CH2), 1.12
(t, J=7.2 Hz, 6H, CH3); 13C NMR (100 MHz, CDCl3): d=
131.66, 128.19, 127.88, 123.27, 84.95, 84.14, 47.22, 41.36,
12.65; GC-MS: m/z=189.
4-[3-(Diethylamino)prop-1-ynyl]benzonitrile
(7b):
1H NMR (400 MHz, CDCl3): d=7.57 (d, J=8.4 Hz, 2H, Ar-
H), 7.48 (d, J=8.4 Hz, 2H, Ar-H), 3.65 (s, 2H, CH2), 2.60
(q, J=7.2 Hz, 4H, CH2), 1.11 (t, J=7.2 Hz, 6H, CH3);
13C NMR (100 MHz, CDCl3): d=132.20, 131.93, 128.24,
118.50, 111.20, 89.58, 83.54, 47.34, 41.44, 12.56; GC-MS:
m/z=212.
4-[3-(Diethylamino)prop-1-ynyl]benzaldehyde
(8b):
Acknowledgements
1H NMR (400 MHz, CDCl3): d=9.99 (s, 1H, CHO), 7.81 (d,
J=8.4 Hz, 2H, Ar-H), 7.55 (d, J=8.0 Hz, 2H, Ar-H), 3.67
(s, 2H, CH2), 2.62 (q, J=7.2 Hz, 4H, CH2), 1.12 (t, J=
7.2 Hz, 6H, CH3); 13C NMR (100 MHz, CDCl3): d=191.47
This work was supported by the Institute of Bioengineering
and Nanotechnology (Biomedical Research Council, Agency
for Science, Technology and Research, Singapore).
168
ꢀ 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2011, 353, 163 – 169