Page 13 of 16
RSC Advances
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3
(
m, 4H), 1.50 – 1.37 (m, 2H); C NMR (62.9 MHz, CDCl ): δ = 138.7, 132.5, 131.8, 128.5, 128.3, 128.0, 127.4, 123.4,
3
8
7.8, 86.1, 62.4, 50.7, 26.2, 24.5.
6
5
N-[1-(4-methoxyphenyl)-3-phenyl-2-propyn-1-yl]-piperidine (4i): Yellow oil. (hexane/EtOAc 85:15, 98%, 299 m
-
1
DOI: 10.1039/C5RA05546F
(
(
(
neat, cm ) υ: 3061 (m), 3034 (m), 2997 (m), 2932 (s), 2853 (s), 2833 (s), 2804 (s), 2748 (m), 1890 (w), 1737 (m), 1688
m), 1610 (s), 1598 (s), 1583 (s), 1504 (s), 1489 (s), 1454 (s), 1443 (s), 1319 (s), 1302 (s), 1247 (s), 1169 (s), 1113 (s), 1092
s), 1068 (m), 1038 (s), 989 (m), 968 (m), 914 (m), 848 (m), 773 (s), 756 (s), 690 (s). H NMR (250 MHz, CDCl ): δ = 7.57
1
3
–
2
2
7.27 (m, 7H), 6.94 – 6.84 (m, 2H), 4.75 (s, 1H), 3.83 (s, 3H), 2.62 – 2.45 (m, 4H), 1.71 – 1.50 (m, 4H), 1.49 – 1.37 (m,
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3
H); C NMR (62.9 MHz, CDCl ): δ = 159.0, 131.8, 130.8, 129.6, 128.3, 128.0, 123.5, 113.4, 87.6, 86.5, 61.8, 55.3, 50.6,
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6.2, 24.5.
7
3
1
(
1
1
7
-(1-(4-bromophenyl)-3-phenylprop-2-yn-1-yl)piperidine (4k): Yellow oil. (hexane/EtOAc 95:5, 94%, 332 mg). IR
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1
neat, cm ) υ: 3053 (m), 2934 (s), 2853 (s), 2833 (s), 2806 (s), 2748 (m), 1902 (w), 1737 (w), 1597 (s), 1583 (m), 1504 (s),
574 (m), 1483 (s), 1466 (m), 1443 (s), 1396 (s), 1317 (m), 1286 (m), 1269 (m), 1202 (m), 1171 (w), 1153 (m), 1113 (m),
092 (s), 1070 (s), 1013 (s), 991 (s), 970 (m), 912 (w), 848 (m), 806 (m), 754 (s), 690 (s). H NMR (250 MHz, CDCl ): δ =
.59 – 7.27 (m, 9H), 4.74 (s, 1H), 2.62 – 2.45 (m, 4H), 1.71 – 1.50 (m, 4H), 1.49 – 1.37 (m, 2H); C NMR (62.9 MHz,
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3
1
3
CDCl ): δ = 137.9, 131.8, 131.2, 130.2, 128.3, 128.2, 123.1, 121.4, 88.3, 85.3, 61.8, 50.7, 26.2, 24.4.
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7
4
-1
1
2
1
-(1-phenylhept-1-yn-3-yl)piperidine (4l): Yellow oil. (hexane/EtOAc 9:1, 88%, 225 mg). IR (neat, cm ) υ: 3055 (w),
932 (s), 2856 (s), 2803 (s), 2748 (w), 2681 (w), 1942 (w), 1597 (m), 1588 (s), 1489 (m), 1466 (m), 1452 (m), 1443 (s),
325 (m), 1304 (w), 1256 (m) 1155 (m), 1116 (m), 1096 (m), 1068 (w), 910 (w), 862 (w), 754 (s), 690 (s). H NMR (250
1
MHz, CDCl ): δ = 7.49 – 7.26 (m, 5H), 3.52 – 3.42 (m, 1H), 2.72 – 2.60 (m, 2H), 2.52 – 2.40 (m, 2H), 1.84 – 1.19 (m, 12H),
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1
3
0
2
.93 (t, J = 7.3 Hz, 3H); C NMR (62.9 MHz, CDCl ): δ = 131.8, 128.2, 127.7, 123.7, 88.3, 85.6, 58.7, 50.6, 33.5, 29.1,
6.2, 24.6, 22.6, 14.1.
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7
4
-1
1
2
1
-(1-phenylethynyl-heptyl)-piperidine (4m): Yellow oil. (hexane/EtOAc 9:1, 88%, 250 mg). IR (neat, cm ) υ: 3055 (w),
932 (s), 2856 (s), 2803 (s), 2748 (w), 2681 (w), 1942 (w), 1597 (m), 1588 (s), 1489 (m), 1466 (m), 1452 (m), 1443 (s),
325 (m), 1304 (w), 1155 (m), 1116 (m), 1096 (m), 1068 (w), 910 (w), 862 (w), 754 (s), 690 (s). H NMR (250 MHz,
1
CDCl ): δ = 7.49 – 7.26 (m, 5H), 3.52 – 3.42 (m, 1H), 2.76 – 2.60 (m, 2H), 2.57 – 2.40 (m, 2H), 1.84 – 1.19 (m, 16H), 0.89
3
1
3
(
t, J = 6.7 Hz, 3H); C NMR (62.9 MHz, CDCl ): δ = 131.8, 128.2, 127.7, 123.7, 88.3, 85.6, 58.7, 50.6, 33.5, 31.8, 29.1,
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2
6.9, 26.2, 24.6, 22.6, 14.1.
-[1-(2-furan-2-yl)-3-phenylprop-2-ynyl]piperidine (4n): Dark, sticky oil. (hexane/EtOAc 85:15, 82%, 216 mg). IR
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4
1
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1
(
(
(
neat, cm ) υ: 3115 (w), 3055 (w), 2934 (m), 2806 (s), 2852 (s), 2748 (m), 1599 (m), 1558 (s), 1489 (s), 1468 (m), 1452
m), 1443 (s), 1317 (m), 1300 (m), 1225 (m), 1206 (m), 1184 (m), 1153 (m), 1142 (m), 1115 (m), 1092 (m), 1070 (w), 1012
1
s), 939 (m), 814 (m), 885 (m), 777 (m), 754 (s), 735 (s), 690 (s). H NMR (250 MHz, CDCl ): δ = 7.54 – 7.46 (m, 2H), 7.45
3
–
7.41 (m, 1H), 7.38 – 7.29 (m, 3H), 6.51 – 6.46 (m, 1H), 6.38 – 6.33 (m, 1H), 4.88 (s, 1H), 2.68 – 2.50 (m, 4H), 1.76 – 1.52
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(m, 4H), 1.51 – 1.36 (m, 2H); C NMR (62.9 MHz, CDCl ): δ = 151.8, 142.6, 131.9, 128.3, 128.3, 123.0, 110.0, 109.2,
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6.4, 83.9, 56.6, 50.6, 26.0, 24.4.
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1
1
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1
‐[1‐(4‐methylphenyl)non‐2‐yn‐1‐yl]piperidine (4o): Yellow oil. (hexane/EtOAc 9:1, 78%, 231 mg). IR (neat, cm ) υ:
051 (m), 3024 (m), 2932 (s), 2855 (s), 2804 (s), 2747 (m), 2257 (w), 1903 (w), 1707 (m), 1604 (w), 1510 (s), 1466 (s),
454 (s), 1443 (s), 1379 (m), 1319 (s), 1296 (s), 1269 (s), 1204 (m), 1175 (m), 1155 (s), 1113 (s), 1088 (s), 1064 (m), 1038
m), 1022 (m), 989 (s), 848 (m), 823 (m), 808 (m), 764 (s), 725 (m), 658 (m). H NMR (250 MHz, CDCl ): δ = 7.42 (d, J =
1
(
3
7
1
2
.6 Hz, 2H), 7.13 (d, J = 7.6 Hz, 2H), 4.49 (s, 1H), 2.52 – 2.36 (m, 4H), 2.34 (s, 3H), 2.31 – 2.24 (m, 4H), 1.66 – 1.23 (m,
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2H), 0.90 (t, J = 6.7 Hz, 3H); C NMR (62.9 MHz, CDCl ): δ = 136.8, 136.3, 128.6, 128.5, 87.7, 61.8, 50.5, 31.4, 29.1,
3
+
8.6, 26.2, 24.5, 22.6, 21.1, 18.8, 14.0. GC-MS (r.t. 19.25 min): m/z (%) = 297 (18) [M] , 282 (1), 226 (8), 212 (10), 206
(
100), 128 (10), 142 (10), 105 (20), 84 (2). Anal. Calcd for C H N (297.4776): C, 84.8; H, 10.5. Found: C, 84.6; H, 10.7.
21 31
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‐[1,3‐bis(4‐methylphenyl)prop‐2‐yn‐1‐yl]piperidine (4p). Yellowish solid. (hexane/EtOAc 9:1, 94%, 285 mg). m.p. 73 –
4 °C. IR (neat, cm ) υ: 3051 (m), 3026 (w), 2932 (m), 2856 (m), 2804 (w), 2747 (w), 1734 (m), 1717 (w), 1684 (w), 1506
1
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1
(s), 1456 (m), 1454 (s), 1443 (s), 1379 (m), 1319 (w), 1271 (m), 1115 (m), 1092 (m), 815 (s), 764 (m). H NMR (250 MHz,
CDCl ): δ = 7.50 (d, J = 7.9 Hz, 2H), 7.40 (d, J = 8.6 Hz, 2H), 7.15 (t, J = 7.9 Hz, 4H), 4.74 (s, 1H), 2.62 – 2.46 (m, 4H),
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3
2
1
3
.36 (s, 6H), 2.31 – 2.24 (m, 4H), 1.66 – 1.50 (m, 4H), 1.49 – 1.35 (m, 2H); C NMR (62.9 MHz, CDCl ): δ = 138.0, 137.0,
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35.8, 131.7, 130.0, 128.7, 128.5, 120.4, 87.6, 85.7, 62.2, 50.7, 26.3, 24.5, 21.4, 21.1. GC-MS (r.t. 18.93 min): m/z (%) =
03 (22) [M] , 288 (2), 219 (100), 212 (28), 203 (14), 189 (8), 165 (4), 129 (6), 91 (1), 65 (2), 41 (2). Anal. Calcd for
+
C H N (303.4406): C, 87.1; H, 8.3. Found: C, 87.3; H, 8.6.
2
2
25
1
7
1
9
7
2
2
‐[1‐(4‐methylphenyl)‐3‐[tris(propan‐2‐yl)silyl]prop‐2‐yn‐1‐yl]piperidine (4q). Pale yellowish oil. (hexane/EtOAc 9:1,
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1
0%, 257 mg). IR (neat, cm ) υ: 2940 (s), 2891 (s), 2864 (s), 2806 (m), 2747 (m), 2158 (m), 1558 (m), 1510 (m), 1464 (s),
443 (m), 1383 (m), 1364 (m), 1317 (m), 1294 (m), 1267 (m), 1202 (m), 1175 (m), 1153 (m), 1113 (m), 1092 (m), 1003 (s),
1
88 (s), 920 (m), 883 (s), 847 (m), 822 (m), 808 (,), 766 (s), 721 (s), 677 (s). H NMR (250 MHz, CDCl ): δ = 7.49 (d, J =
3
.9 Hz, 2H), 7.14 (d, J = 7.9 Hz, 2H), 4.63 (s, 1H), 2.55 – 2.40 (m, 4H), 2.34 (s, 3H), 1.65 – 1.48 (m, 4H), 1.47 – 1.33 (m,
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H), 1.19 – 1.02 (m, 21H); C NMR (62.9 MHz, CDCl ): δ = 136.9, 135.8, 128.6, 128.4, 103.8, 87.9, 62.3, 50.3, 26.3, 24.6,
3
+
1.1, 18.8, 11.4. GC-MS (r.t. 20.46 min): m/z (%) = 369 (10) [M] , 326 (2), 278 (67), 212 (16), 207 (100), 191 (12), 159
(
16), 157 (6), 133 (10), 111 (10), 96 (10), 84 (8), 73 (12). Anal. Calcd for C H NSi (369.6587): C, 79.0; H, 10.6. Found: C,
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8.7; H, 10.4.
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1
Dibutyl(1‐phenylhex‐1‐yn‐3‐yl)amine (4r): Yellow oil. (hexane/EtOAc 95:5, 92%, 262 mg). IR (neat, cm ) υ: 3055 (w),
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1
957 (s), 2930 (s), 2872 (s), 2816 (m), 1944 (w), 1489 (s), 1466 (s), 1456 (m), 1443 (m), 1377 (m), 1310 (m), 1273 (m),
250 (m), 1173 (m), 1113 (m), 1090 (m), 1070 (m), 1028 (m), 910 (m), 883 (s), 756 (s), 690 (s). H NMR (250 MHz,
1