Page 17 of 24
New Journal of Chemistry
Please do not adjust margins
Journal Name
ARTICLE
1
2
3
4
163.26, 161.30, 134.54, 131.86, 130.06, 128.28, 123.25, 61.71,
50.66, 26.24, 24.49.
DOI: 10.1039/D0NJ03081C
26.30, 24.62, 15.01. Anal. Calc. For C26H33NO; C, 83.15; H, 8.86; N,
5
6
7
8
1-(1-(3-nitrophenyl)-3-phenylprop-2-yn-1-yl)piperidine (7am)53:
Yellow liquid, Yield: Cat. 1 (252.8mg, 79%), Cat. 2 (262.4%, 82%), Cat.
3 (256mg, 80%), Cat. 4 (259.2mg, 81%).1H NMR (400 MHz, CDCl3) δ
8.56 (s, 1H), 8.16 (d, J = 8.1 Hz, 1H), 8.02 (d, J = 7.7 Hz, 1H), 7.55 (t, J
= 3.0 Hz, 2H), 7.54 (d, J = 3.7 Hz, 1H), 7.52 (d, J = 7.9 Hz, 2H), 4.88 (s,
1H), 2.56-2.53 (m, 4H), 1.64-1.59 (m, 4H), 1.49-1.45(m, 2H). 13C NMR
(101 MHz, CDCl3) δ 148.40, 141.46, 134.56, 131.98, 128.53, 123.47,
122.75, 89.23, 84.24, 61.78, 50.79, 26.21, 24.38.
3.73. Found: C, 83.01; H, 8.72; N, 3.78.
1-(3-(4-(tert-butyl)phenyl)-1(4methoxyphenyl)prop-2-yn-1-
yl)piperidine (8ac): Yellow liquid, Yield: Cat. 1 (332.12mg, 92%), Cat.
2 (350.12mg, 97%), Cat. 3 (342.95, 95%), Cat. 4 (346.56mg, 96%).1H
NMR (400 MHz, CDCl3) 7.57 (d, J = 8.6 Hz, 2H), 7.49 (d, J = 6.7 Hz, 2H),
7.39 (d, J = 8.5 Hz, 1H), 7.03 (d, J = 8.7 Hz, 1H), 6.91 (d, J = 8.7 Hz, 2H),
4.78 (s, 1H), 3.83 (s, 1H), 2.61 – 2.57 (m, 4H), 1.62-1.59 (m, 4H), 1.48
– 1.45 (m, 2H), 1.35 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 164.71,
159.07, 151.35, 132.10, 131.64, 130.89, 129.80, 125.45, 120.51,
114.34, 113.39, 87.83, 85.75, 61.94, 55.65, 55.28, 50.48, 34.85,
31.27, 26.30. Anal. Calc. For C25H31NO; C, 83.06; H, 8.64; N, 3.87.
Found: C, 83.17; H, 8.51; N, 3.74.
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
1-(1-(naphthalen-2-yl)-3-phenylprop-2-yn-1-yl)piperidine (7an)50:
Yellow liquid, Yield: Cat. 1 (289.25mg, 89%), Cat. 2 (299mg, 92%),
1
Cat. 3 (292.5mg, 90%), Cat. 4 (295.75mg, 91%). H NMR (400 MHz,
CDCl3) δ 8.60 (d, J = 9.2 Hz, 1H), 8.13 (d, J = 7.4 Hz, 1H), 7.97 (d, J =
10.7 Hz, 2H), 7.72 (d, J = 9.0 Hz, 2H), 7.68 (d, J = 8.4 Hz, 1H), 7.62 (d,
J = 7.6 Hz, 3H), 7.46 (d, J = 6.7 Hz, 2H), 5.61 (s, 1H), 2.84-2.81 (m, 4H),
1.77 – 1.66 (m, 4H), 1.62 – 1.58 (m, 2H). 13C NMR (101 MHz, CDCl3) δ
134.44, 132.18, 128.97, 128.33, 127.15, 125.95, 125.33, 125.06,
123.75, 88.91, 86.24, 60.83, 50.99, 26.60, 24.92.
1-(1-phenyl-3-(p-tolyl)prop-2-yn-1-yl)piperidine (8ad): Yellow
liquid, Yield: Cat. 1 (260.1mg, 90%), Cat. 2 (274.5mg, 95%), Cat. 3
(268.7mg, 93%), Cat. 4 (271.6mg, 94%).1H NMR (500 MHz, CDCl3) δ
7.73 (d, J = 7.7 Hz, 2H), 7.43 (d, J = 7.1 Hz, 2H), 7.36 (d, J = 7.2 Hz, 2H),
7.21 (d, J = 7.6 Hz, 2H), 4.88 (s, 1H), 2.62-2.40(m, 4H), 1.71 – 1.66 (m,
4H), 1.49-1.43 (m, 2H). 13C NMR (126 MHz, CDCl3) δ 138.83, 138.13,
131.77, 129.79, 129.26, 129.21, 128.11, 127.47, 120.38, 115.00,
88.01, 85.39, 62.49, 50.78, 26.29, 24.55, 21.53. Anal. Calc. For
C21H23N; C, 87.15; H, 8.01; N, 4.84. Found: C, 87.27; H, 8.15; N, 4.42.
4-(3-(4-(tert-butyl)phenyl)-1-(piperidin-1-yl)prop-2-yn-1-yl)-N,N-
diethylaniline (8ae): Yellow liquid, Yield: Cat. 1 (357.78mg, 89%),
Cat. 2 (369.84mg, 92%), Cat. 3 (361.8mg, 90%), Cat. 4 (356.82mg,
91%).1H NMR (400 MHz, CDCl3) δ 7.44 (d, J = 4.0 Hz, 4H), 7.35 (d, J =
8.4 Hz, 2H), 6.66 (d, J = 8.8 Hz, 2H), 4.69 (s, 1H), 3.36 (q, J = 7.0 Hz,
4H), 2.64 – 2.50 (m, 4H), 1.59-1.57 (m, 4H), 1.46 – 1.41 (m, 2H), 1.33
(s, 9H), 1.17 ( t, J = 6.1 Hz, 6H). 13C NMR (126 MHz, CDCl3) δ 151.01,
147.23, 131.50, 129.66, 128.24, 125.19, 120.71, 111.61, 111.29,
87.10, 86.47, 61.92, 44.38, 31.22, 26.24, 24.59, 12.65. Anal. Calc. For
C28H38N2; C, 83.53; H, 9.51; N, 6.96. Found: C, 83.47; H, 9.57; N, 6.91.
4-(3-(4-(tert-butyl)phenyl)-1-(piperidin-1-yl)prop-2-yn-1-yl)-N,N-
dimethylaniline (8af): Yellow liquid, Yield: Cat. 1 (288.84mg, 87%),
Cat. 2 (298.8mg, 90%), Cat. 3 (292.16mg, 88%), Cat. 4 (295.48mg,
89%).1H NMR (400 MHz, CDCl3) δ 7.75 (d, J = 9.0 Hz, 2H), 7.46 (d, J =
8.8 Hz, 1H), 7.38 (d, J = 8.1 Hz, 1H), 7.29 (d, J = 8.8 Hz, 2H), 7.11 (d, J
= 8.1 Hz, 1H), 6.71 (d, J = 3.9 Hz, 1H), 5.05 (s, 1H), 3.09 (m, 4H), 2.95
(s, 3H), 2.91 (s, 6H), 1.61-1.59 (m, 4H), 1.46 – 1.39 (m, 2H). 13C NMR
(101 MHz, CDCl3) δ 150.13, 149.53, 138.02, 137.65, 131.68, 130.81,
129.64, 129.00, 128.52, 121.02, 120.51, 112.91, 112.14, 111.08,
1-(3-phenylprop-2-yn-1-yl)piperidine (7ao)85: Yellow liquid, Yield:
Cat. 1 (173.13mg, 87%), Cat. 2 (179.1mg, 90%), Cat. 3 (175.12mg,
88%), Cat. 4 (179.1mg, 90%). 1H NMR (400 MHz, CDCl3 ) δ 7.43 (d, J
= 6.6Hz, 2H), 7.29 (t, J = 4.2, Hz, 3H), 3.47 (s, 1H), 2.57-2.56 (m, 4H),
1.66-1.61 (m, 4H), 1.45-1.44 (m, 2H). 13C NMR (101 MHz, CDCl3) δ
131.79, 128.28, 128.04, 123.38, 85.10, 53.53, 48.55, 26.02, 24.02.
1-(3-(4-(tert-butyl)phenyl)-1-phenylprop-2-yn-1-yl)piperidine
(8aa)86: Yellow oily liquid, Yield: Cat. 1 (304.52mg, 92%), Cat. 2
(317.76mg, 96%), Cat. 3 (311.14mg, 94%), Cat. 4 (314.45mg, 95%).1H
NMR (500 MHz, CDCl3) δ 7.78 (d, J = 7.7 Hz, 2H), 7.60 (d, J = 7.6 Hz,
2H), 7.46 (d, J = 6.7 Hz, 4H), 7.38 (d, J = 6.5 Hz, 1H), 4.92 (s, 1H), 2.70-
2.69 (m, 4H), 1.71-1.70 (m, 4H), 1.56-1.55(m, 2H), 1.43 (s, 9H). 13
C
NMR (126 MHz, CDCl3) δ 151.35, 138.94, 131.71, 128.68, 128.33,
127.52, 126.06, 125.60, 125.38, 120.55, 115.00, 88.13, 85.45, 62.55,
50.79, 34.84, 31.34, 26.37, 24.64.
1-(3-(4-(tert-butyl)phenyl)-1-(4ethoxyphenyl)prop-2-yn-1
yl)piperidine (8ab): Yellow liquid, Yield: Cat. 1 (348.75mg, 93%), Cat.
2 (367.5mg, 98%), Cat. 3 (360mg, 96%), Cat. 4 (363.75mg, 97%).1H
NMR (400 MHz, CDCl3) δ 7.57 (d, J = 8.6 Hz, 2H), 7.50 (d, J = 8.5 Hz,
2H), 7.38 (d, J = 8.5 Hz, 2H), 6.91 (d, J = 8.7 Hz, 2H), 4.77 (s, 1H), 4.05
(q, J = 7.0 Hz, 2H), 2.59-2.58 (s, 4H), 1.64-1.61(m, 4H), 1.48-1.46 (m,
2H), 1.44 (t, J = 5.6 Hz, 3H), 1.35 (s, 9H). 13C NMR (101 MHz, CDCl3) δ
158.44, 151.32, 132.11, 131.61, 130.72, 129.79, 125.39, 120.53,
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 17
Please do not adjust margins