Organic & Biomolecular Chemistry
Paper
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NMR (500 MHz, CDCl3) δ 7.72–6.98 (m, 5H), 5.38 (s, 1H), 3.58 acetate = 5 : 1 H NMR (500 MHz, CDCl3) δ 7.49–7.36 (m, 5H),
(s, 2H), 2.95 (s, 2H), 2.57 (t, J = 5.4 Hz, 2H), 2.08 (d, J = 0.6 Hz, 6.39–6.35 (m, 1H), 3.71 (s, 2H), 3.17 (dt, J = 5.9, 2.9 Hz, 2H),
2H), 1.70 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 138.5, 132.7, 2.73 (t, J = 5.7 Hz, 2H), 2.44–2.38 (m, 2H). 13C NMR (126 MHz,
129.3, 128.2, 127.0, 119.4, 62.9, 53.0, 50.0, 30.9, 23.0. HRMS CDCl3) δ 137.9, 129.0, 128.4, 127.3, 126.8 (q, J = 31.0 Hz),
(ESI) m/z calculated for C13H18N [M + H]+: 188.1434, found: 124.8, 122.6, 62.2, 51.5, 48.5, 23.3. 19F NMR (471 MHz, CDCl3)
188.1435.
1-Butyl-1,2,3,6-tetrahydropyridine (10g). Colorless oil, 88% 242.1151, found: 242.1154.
yield. Eluent: petroleum ether/ethyl acetate = 5 : 1 1H NMR
1-Benzyl-2,5-dimethyl-1,2,3,6-tetrahydropyridine (10n). Colorless
δ −69.4. HRMS (ESI) m/z calculated for C13H15F3N [M + H]+:
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(500 MHz, CD3OD) δ 5.88–5.82 (m, 1H), 5.72–5.67 (m, 1H), oil, 41% yield. Eluent: petroleum ether/ethyl acetate = 5 : 1 H
3.33 (s, 2H), 2.94 (t, J = 6.0 Hz, 2H), 2.74 (t, J = 8.1 Hz, 2H), NMR (500 MHz, CD3OD) δ 7.39–7.25 (m, 5H), 5.45–5.41 (m,
2.34–2.29 (m, 2H), 1.66–1.58 (m, 2H), 1.38 (dd, J = 15.0, 7.5 Hz, 1H), 3.69 (dd, J = 181.7, 12.6 Hz, 2H), 2.97–2.81 (m, 3H),
2H), 0.97 (d, J = 7.4 Hz, 3H). 13C NMR (126 MHz, CD3OD) δ 2.33–2.25 (m, 1H), 1.96–1.88 (m, 1H), 1.59 (s, 3H), 1.15 (d, J =
126.4, 123.7, 58.5, 52.6, 50.7, 28.6, 25.3, 21.5, 14.2. HRMS (ESI) 6.6 Hz, 3H). 13C NMR (126 MHz, CD3OD) δ 138.5, 131.7, 130.9,
m/z calculated for C9H18N [M + H]+: 140.1434, found: 140.1435. 129.4, 128.6, 119.6, 58.3, 53.7, 52.6, 32.8, 20.9, 15.4. HRMS
1-Benzyl-4-propyl-1,2,3,6-tetrahydropyridine (10h). Yellow (ESI) m/z calculated for C14H20N [M + H]+: 202.1590, found:
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oil, 90% yield. Eluent: petroleum ether/ethyl acetate = 5 : 1 H 202.1591.
NMR (500 MHz, CD3OD) δ 7.35–7.23 (m, 5H), 5.36–5.33 (m,
1-Benzyl-2,4,6-trimethyl-1,2,3,6-tetrahydropyridine (10o). Yellow
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1H), 3.56 (s, 2H), 2.94–2.91 (m, 2H), 2.57 (t, J = 5.9 Hz, 2H), oil, 30% yield. Eluent: petroleum ether/ethyl acetate = 5 : 1 H
2.10–2.05 (m, 2H), 1.95 (t, J = 7.6 Hz, 2H), 1.43 (dq, J = 14.9, 7.5 NMR (500 MHz, CD3OD) δ 7.38–7.18 (m, 5H), 5.27 (s, 1H), 3.69
Hz, 2H), 0.89 (t, J = 7.4 Hz, 3H). 13C NMR (126 MHz, CD3OD) δ (d, J = 13.4 Hz, 1H), 3.56 (d, J = 12.3 Hz, 1H), 3.11 (d, J = 28.1
138.2, 137.6, 130.8, 129.3, 128.4, 119.4, 63.6, 53.6, 50.8, 40.0, Hz, 2H), 2.06 (d, J = 17.4 Hz, 1H), 1.76 (d, J = 18.0 Hz, 1H), 1.68
29.4, 21.6, 14.2. HRMS (ESI) m/z calculated for C15H22N [M + (s, 3H), 1.16–1.07 (m, 6H). 13C NMR (126 MHz, CD3OD) δ
H]+: 216.1747, found: 216.1750.
132.2, 130.2, 129.2, 127.9, 125.3, 53.0, 36.3, 32.2, 30.1, 23.4,
1,4-Dibenzyl-1,2,3,6-tetrahydropyridine (10i). Yellow oil, 85% 19.9, 14.7. HRMS (ESI) m/z calculated for C15H22N [M + H]+:
yield. Eluent: petroleum ether/ethyl acetate = 5 : 1 1H NMR 216.1747, found: 216.1749.
(500 MHz, CDCl3) δ 7.48–7.26 (m, 10H), 5.49 (s, 1H), 3.67 (s,
1-Benzyl-4-vinyl-1,2,3,6-tetrahydropyridine (10p). Yellow oil,
2H), 3.40 (s, 2H), 3.09 (s, 2H), 2.64 (t, J = 5.8 Hz, 2H), 2.16 (s, 70% yield. Eluent: petroleum ether/ethyl acetate = 5 : 1 1H
2H). 13C NMR (126 MHz, CDCl3) δ 139.5, 138.3, 135.8, 129.1, NMR (500 MHz, CD3OD) δ 7.42–7.24 (m, 5H), 6.45–6.33 (m,
129.0, 128.2, 128.2, 127.0, 126.0, 120.8, 62.7, 52.9, 49.9, 43.5, 1H), 5.70 (s, 1H), 5.11 (dd, J = 17.5, 7.2 Hz, 1H), 5.00–4.93 (m,
28.9. HRMS (ESI) m/z calculated for: C19H22N [M + H]+: 1H), 3.62 (d, J = 7.7 Hz, 2H), 3.08 (s, 2H), 2.72–2.60 (m, 2H),
264.1747, found: 264.1748.
2.30 (s, 2H). 13C NMR (126 MHz, CD3OD) δ 139.6, 138.1, 135.8,
1-Benzyl-4-(tert-butyl)-1,2,3,6-tetrahydropyridine (10j). Yellow 130.8, 129.4, 128.5, 126.7, 111.7, 63.5, 53.7, 50.4, 25.3. HRMS
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oil, 90% yield. Eluent: petroleum ether/ethyl acetate = 5 : 1 H (ESI) m/z calculated for C14H18N [M + H]+: 200.1434, found:
NMR (500 MHz, CDCl3) δ 7.38–7.30 (m, 4H), 7.27–7.25 (m, 1H), 200.1436.
5.43–5.40 (m, 1H), 3.58 (s, 2H), 3.02 (dd, J = 5.7, 2.6 Hz, 2H),
Ethyl 1-benzyl-1,2,3,6-tetrahydropyridine-4-carboxylate (10q).
2.53 (t, J = 5.7 Hz, 2H), 2.19–2.15 (m, 2H), 1.03 (s, 9H). 13C Yellow oil, 82% yield. Eluent: petroleum ether/ethyl acetate =
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NMR (126 MHz, CDCl3) δ 144.1, 138.3, 129.2, 128.1, 127.0, 5 : 1 H NMR (500 MHz, CDCl3) δ 7.42–7.28 (m, 5H), 6.95–6.91
115.7, 62.8, 53.4, 50.1, 34.8, 28.8, 25.4. HRMS (ESI) m/z calcu- (m, 1H), 4.25 (q, J = 7.1 Hz, 2H), 3.65 (s, 2H), 3.17 (dd, J = 6.3,
lated for: C16H24N [M + H]+: 230.1903, found: 230.1906.
3.0 Hz, 2H), 2.66 (t, J = 5.8 Hz, 2H), 2.50–2.46 (m, 2H), 1.33 (t, J
1-Benzyl-4-(benzyloxy)-1,2,3,6-tetrahydropyridine (10k). Yellow = 7.2 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 166.4, 137.9,
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oil, 85% yield. Eluent: petroleum ether/ethyl acetate = 5 : 1 H 136.4, 128.8, 128.7, 128.2, 127.0, 62.2, 60.1, 52.5, 49.2, 25.2,
NMR (500 MHz, CD3OD) δ 7.37–7.23 (m, 10H), 4.73 (s, 2H), 14.2. HRMS (ESI) m/z calculated for C15H20NO2 [M + H]+:
4.71 (t, J = 3.4 Hz, 1H), 3.59 (s, 2H), 3.01 (dd, J = 5.4, 2.1 Hz, 246.1489, found: 246.1491.
2H), 2.64 (t, J = 6.0 Hz, 2H), 2.25 (t, J = 6.0 Hz, 2H). 13C NMR
1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxamide (10r). Yellow
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(126 MHz, CD3OD) δ 154.1, 138.8, 138.4, 130.7, 129.3, 128.7, oil, 75% yield. Eluent: petroleum ether/ethyl acetate = 5 : 1 H
128.5, 128.5, 93.5, 69.8, 63.1, 52.2, 50.7, 29.0. HRMS (ESI) m/z NMR (500 MHz, CD3OD) δ 6.74 (s, 1H), 3.63 (d, J = 17.4 Hz,
calculated for C19H22NO [M + H]+: 280.1696, found: 280.1698.
1H), 3.47 (d, J = 17.1 Hz, 1H), 2.96–2.89 (m, 2H), 2.56 (s, 3H),
1-Benzyl-5-chloro-1,2,3,6-tetrahydropyridine (10l). Yellow oil, 2.96–2.89 (m, 2H). 13C NMR (126 MHz, CD3OD) δ 170.8, 131.7,
67% yield. Eluent: petroleum ether/ethyl acetate = 5 : 1 1H NMR 129.8, 58.3, 56.0, 48.9, 23.1. HRMS (ESI) m/z calculated for
(500 MHz, CDCl3) δ 7.41–7.27 (m, 1H), 5.91–5.88 (m, 1H), 3.66 C7H13N2O [M + H]+: 141.1022, found: 141.1022.
(s, 2H), 3.15 (dd, J = 4.5, 2.6 Hz, 2H), 2.61 (t, J = 5.7 Hz, 2H),
N-(1-Benzyl-4-methyl-1,2,5,6-tetrahydropyridin-3-yl) acetamide
2.27–2.23 (m, 2H). 13C NMR (126 MHz, CDCl3) δ 137.8, 129.0, (10s). Yellow oil, 85% yield. Eluent: petroleum ether/ethyl
128.8, 128.4, 127.3, 122.6, 61.7, 57.4, 48.4, 26.3. HRMS (ESI) m/z acetate = 5 : 1 1H NMR (500 MHz, CD3OD) δ 7.40–7.20 (m, 5H),
calculated for: C12H15ClN [M + H]+: 208.0888, found: 208.0888.
1-Benzyl-4-(trifluoromethyl)-1,2,3,6-tetrahydropyridine
3.58 (s, 2H), 3.00–2.89 (m, 2H), 2.60 (t, J = 5.9 Hz, 2H), 2.17 (t, J
= 5.4 Hz, 2H), 1.96 (s, 3H), 1.59 (s, 3H). 13C NMR (126 MHz,
(10m). Yellow oil, 72% yield. Eluent: petroleum ether/ethyl CD3OD) δ 170.3, 138.2, 130.8, 129.4, 128.5, 127.2, 125.4, 63.1,
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