Dalton Transactions
Paper
DCM. The organic layer was dried over MgSO4 and filtered. (1.01 g) yield was obtained in the first and second step,
The solvent was evaporated under reduced pressure to give the respectively. 1H NMR (400 MHz, CDCl3, 298 K): δ 8.61–8.52 (m,
crude product as a white solid, which was further purified by 1H), 7.63 (td, J = 7.8, 1.8 Hz, 1H), 7.39–7.29 (m, 5H), 7.24 (d,
silica gel column chromatography (0.32 g, 61% yield). 1H NMR J = 6.8 Hz, 1H), 7.18–7.13 (m, 1H), 3.93 (s, 2H), 3.84 (s, 2H),
(400 MHz, CDCl3, 298 K): δ 8.49 (ddd, J = 4.8, 1.8, 0.8 Hz, 1H), 2.19 (s, 1H). 13C NMR (100 MHz, CDCl3, 298 K): δ 159.9, 149.4,
7.64 (td, J = 7.8, 1.8 Hz, 1H), 7.58–7.51 (m, 6H), 7.46 (d, J = 7.8 140.2, 136.5, 128.5, 128.4, 127.1, 122.4, 122.0, 54.6, 53.6. FTIR
Hz, 1H), 7.31–7.24 (m, 6H), 7.21–7.16 (m, 3H), 7.12 (ddd, J = (KBr, cm−1): 3313 (ν (N–H)), 3061, 3027, 2920, 2838, 1952,
7.6, 4.8, 1.2 Hz, 1H), 3.52 (s, 2H), 2.59 (s, 1H). 13C NMR 1591, 1454, 1433, 1362, 1120, 994, 753, 699. HRMS-ESI (m/z):
(100 MHz, CDCl3, 298 K): δ 160.5, 149.2, 146.1, 136.6, 128.8, [M + H]+ calcd for C14H17N2, 199.1235; found, 199.1231.
128.0, 126.5, 122.0, 121.8, 71.2, 49.7. FTIR (KBr, cm−1): 3313
2-(1-(1-Methylethylamino)methyl)pyridine, L6H. Using the
(ν (N–H)), 3054, 2923, 1956, 1592, 1569, 1428, 1354, 1109, similar procedure established for the synthesis of L1H, L6H
1031, 773, 708. HRMS-ESI (m/z): [M + H]+ calcd for C25H23N2, was obtained as a pale yellow solid. 92% (4.07 g) and 66%
351.1861; found, 351.1854.
(1.34 g) yield was obtained in the first and second step,
2-(1-(Diphenylmethylamino)methyl)pyridine, L2H. Using the respectively. 1H NMR (400 MHz, CDCl3, 298 K): δ 8.55 (ddd, J =
similar procedure established for the synthesis of L1H, L2H 5.0, 1.8, 1.0 Hz, 1H), 7.70 (td, J = 7.8, 1.8 Hz, 1H), 7.60 (dt, J =
was obtained as a pale yellow solid. 88% (2.54 g) and 74% 7.8, 1.2 Hz, 1H), 7.23 (ddd, J = 7.6, 4.8, 1.2 Hz, 1H), 4.20 (s,
(1.51 g) yield was obtained in the first and second step, 2H), 3.21 (hept, J = 6.6 Hz, 1H), 1.36 (d, J = 6.6 Hz, 6H). 13C
respectively. 1H NMR (400 MHz, CDCl3, 298 K): δ 8.54 (ddd, J = NMR (100 MHz, CDCl3, 298 K): δ 153.4, 149.4, 137.3, 123.8,
4.8, 1.8, 1.0 Hz, 1H), 7.61 (td, J = 7.6, 1.8 Hz, 1H), 7.47–7.40 (m, 123.4, 49.5, 49.5, 20.3. FTIR (KBr, cm−1): 3312 (ν (N–H)), 2964,
4H), 7.33–7.25 (m, 5H), 7.23–7.17 (m, 2H), 7.14 (ddd, J = 7.6, 2926, 2854, 1592, 1570, 1473, 1434, 1174, 995, 756. HRMS-ESI
4.8, 1.2 Hz, 1H), 4.87 (s, 1H), 3.87 (s, 2H), 2.52 (s, 1H). 13C (m/z): [M + H]+ calcd for C9H15N2, 151.1235; found, 151.1230.
NMR (100 MHz, CDCl3, 298 K): δ 159.8, 149.4, 143.9, 136.4,
2-(1-(Cyclohexylamino)methyl)pyridine, L7H. Using the
128.6, 127.5, 127.1, 122.6, 122.0, 77.5, 53.5. FTIR (KBr, cm−1): similar procedure established for the synthesis of L1H, L7H
3325 (ν (N–H)), 3044, 2818, 1958, 1591, 1566, 1450, 1342, 1149, was obtained as a pale yellow solid. 93% (5.70 g) and 94%
993, 743, 704. HRMS-ESI (m/z): [M + H]+ calcd for C19H19N2, (1.78 g) yield was obtained in the first and second step,
275.1548; found, 275.1546.
1
respectively. H NMR (400 MHz, CDCl3, 298 K): δ 8.54 (dt, J =
4.8, 1.2 Hz, 1H), 7.63 (td, J = 7.6, 1.8 Hz, 1H), 7.32–7.28 (m,
2-Methyl-6-(1-(diphenylmethylamino)methyl)pyridine, L3Me
.
Using the similar procedure established for the synthesis of 1H), 7.14 (ddd, J = 7.4, 4.8, 1.2 Hz, 1H), 3.93 (s, 2H), 2.54–2.44
L1H, L3H was obtained as a pale yellow solid. 68% (1.10 g) and (m, 1H), 2.15 (s, 1H), 1.924 (ddt, J = 9.8, 3.8, 1.8 Hz, 2H), 1.74
99% (1.00 g) yield was obtained in the first and second step, (dt, J = 12.2, 3.6 Hz, 2H), 1.65–1.57 (m, 1H), 1.31–1.09 (m, 5H).
1
respectively. H NMR (400 MHz, CDCl3, 298 K): δ 7.52 (s, 1H), 13C NMR (100 MHz, CDCl3, 298 K): δ 160.2, 149.3, 136.5, 122.4,
7.48–7.42 (m, 4H), 7.30 (t, J = 7.6 Hz, 4H), 7.22 (d, J = 7.4 Hz, 121.9, 56.7, 52.5, 33.6, 26.2, 25.1. FTIR (KBr, cm−1): 3310
2H), 7.08 (d, J = 7.6 Hz, 1H), 7.01 (d, J = 7.6 Hz, 1H), 4.88 (s, (ν (N–H)), 3065, 3009, 2926, 2852, 1592, 1570, 1433, 1371,
1H), 3.83 (s, 2H), 2.53 (s, 3H). 13C NMR (100 MHz, CDCl3, 1126, 1048, 755. HRMS-ESI (m/z): [M + H]+ calcd for C13H18N2,
298 K): δ 159.1, 158.1, 144.1, 136.7, 128.6, 127.6, 127.1, 121.5, 191.1548; found, 191.2980.
119.4, 77.5, 77.2, 76.8, 67.2, 53.6, 24.6. FTIR (KBr, cm−1): 3319
2-(1-(4-Methoxyphenylmethylamino)methyl)pyridine, L8H.
(ν (N–H)), 3060, 3025, 2921, 2829, 1953, 1593, 1577, 1492, Using the similar procedure established for the synthesis of
1452, 1342, 1117, 1028, 753, 702. HRMS-ESI (m/z): [M + H]+ L1H, L8H was obtained as a pale yellow solid. 73% (3.10 g) and
calcd for C20H21N2, 289.1705; found, 289.1701.
91% (0.31 g) yield was obtained in the first and second step,
2-(1-(1-Phenylethylamino)methyl)pyridine, L4H. Using the respectively. 1H NMR (400 MHz, CDCl3, 298 K): δ 8.59–8.51 (m,
similar procedure established for the synthesis of L1H, L4H 1H), 7.64 (tt, J = 7.6, 1.8 Hz, 1H), 7.35–7.19 (m, 3H), 7.15 (ddd,
was obtained as a pale yellow solid. 92% (2.00 g) and 80% J = 7.6, 4.8, 1.2 Hz, 1H), 6.92–6.81 (m, 2H), 3.91 (s, 2H), 3.79 (s,
(0.67 g) yield was obtained in the first and second step, 3H), 3.78 (s, 2H), 2.14 (s, 1H). 13C NMR (100 MHz, CDCl3,
1
respectively. H NMR (400 MHz, CDCl3, 298 K): δ 8.55 (d, J = 298 K): δ 159.9, 158.8, 149.4, 136.5, 132.4, 129.6, 122.5, 122.0,
4.8 Hz, 1H), 7.60 (td, J = 7.8, 1.8 Hz, 1H), 7.40–7.30 (m, 4H), 113.9, 55.4, 54.6, 53.0. FTIR (KBr, cm−1): 3312 (ν (N–H)), 3007,
7.26–7.22 (m, 1H), 7.20 (d, J = 7.8 Hz, 1H), 7.14 (ddd, J = 7.6, 2934, 2835, 2058, 1884, 1611, 1510, 1301, 1247, 1176, 1034,
4.8, 1.2 Hz, 1H), 3.83 (q, J = 6.6 Hz, 1H), 3.75 (s, 2H), 2.19 (s, 816, 758. HRMS-ESI (m/z): [M + H]+ calcd for C14H17N2O,
1H), 1.42 (d, J = 6.6 Hz, 3H). 13C NMR (100 MHz, CDCl3, 229.1341; found, 229.1335.
298 K): δ 159.9, 149.4, 145.5, 136.5, 128.6, 127.1, 126.9, 122.6,
2-(1-(4-Trifluoromethylphenylmethylamino)methyl)pyridine,
122.0, 58.2, 53.2, 24.6. FTIR (KBr, cm−1): 3317 (ν (N–H)), 3066, L9H. Using the similar procedure established for the synthesis
2964, 2925, 1950, 1591, 1450, 1433, 1369, 1128, 994, 761, 701. of L1H, L9H was obtained as a pale yellow solid. 79% (3.9 g)
HRMS-ESI (m/z): [M + H]+ calcd for C14H17N2, 213.1392; found, and 93% (0.93 g) yield was obtained in the first and second
213.1387.
1
step respectively. H NMR (400 MHz, CDCl3, 298 K): δ 8.57 (dt,
2-(1-(Phenylmethylamino)methyl)pyridine, L5H. Using the J = 5.0, 1.4 Hz, 1H), 7.64 (td, J = 7.6, 1.8 Hz, 1H), 7.58 (d, J = 8.0
similar procedure established for the synthesis of L1H, L5H Hz, 2H), 7.49 (d, J = 8.0 Hz, 2H), 7.29 (d, J = 7.8 Hz, 1H), 7.17
was obtained as a pale yellow solid. 68% (2.5 g) and 62% (m, J = 7.6, 4.8, 1.2 Hz, 1H), 3.92 (s, 2H), 3.91 (s, 2H), 2.13 (s,
This journal is © The Royal Society of Chemistry 2019
Dalton Trans.