10.1002/adsc.201800504
Advanced Synthesis & Catalysis
1232, 1265, 1292, 1324, 1360, 1392, 1453, 1470, 1508,
1607, 1715, 2832, 2959, 3034, 3380; H NMR (400 MHz,
1
N-2-Methylphenylmorpholine:[31] yellow solid; mp
28.4__28.6 °C (lit. [31] 37__38 °C); IR (neat) 532, 642, 693,
710, 775, 846, 876, 936, 952, 991, 1066, 1122, 1189, 1244,
1264, 1301, 1337, 1364, 1379, 1447, 1494, 1581, 1601,
CDCl3), δ = 1.20 (s, 9H), 3.69 (s, 3H), 6.75 (dt, 2H), 6.77
(d, 2H), 6.94 (d, 2H). 7.14 (dt, 2H); 13C NMR (100 MHz,
CDCl3) δ = 31.5, 34.0, 55.6, 114.6, 115.8, 121.4, 126.0,
128.3, 136.3, 142.4, 142.6, 154.8; HRMS [DART+]. m/z
calcd for C17H22NO: 256.1701 [M+H]+, Found: 256.1700
[M+H]+.
1
2827, 2851, 2887, 2966; H NMR (400 MHz, CDCl3) δ =
2.36 (s, 3H), 3.17 (t, 4H), 3.88 (t, 4H), 6.77 (m, 3H), 7.22
(t, 1H); 13C NMR (100 MHz, CDCl3) δ = 21.7, 49.4, 66.9,
112.8, 116.4, 120.9, 128.9, 138.8, 151.3.
Ethyl-4-anilinobenzoate:[30]
cololess
solid;
mp
109.1__109.4 °C (lit. [30] 111 °C); IR (neat) 582, 693, 750,
768, 806, 845, 960, 1019, 1109, 1173, 1249, 1271, 1334,
1364, 1407, 1475, 1495, 1528, 1587, 1676, 1687, 2965,
3338, 3365; 1H NMR (400 MHz, CDCl3), δ = 1.38 (t, 3H),
4.33 (q, 2H), 7.00 (d, 2H), 7.06 (t, 1H), 7.17 (d, 2H), 7.33
N-(2-Methylphenyl)-2,6-dimethylaniline:[42] pale brown
liquid; IR (neat) 557, 627, 691, 731, 766, 851, 909, 994,
1034, 1093, 1164, 1216, 1261, 1.09, 1376, 1474, 1502,
1586, 1606; 1H NMR (400 MHz, CDCl3), δ = 2.21 (s, 6H),
2.25 (s, 3H), 5.1 (br s, 1H), 6.30 (d, 1H), 6.35 (s, 1H), 6.57
(t, 2H), 7.92 (d, 2H); 13C NMR (100 MHz, CDCl3) δ =14.4, (d, 1H), 7.02-7.14 (m, 4H); 13C NMR (100 MHz, CDCl3) δ
60.4, 114.5, 120.2, 121.3, 123.0, 129.4, 131.3, 140.9, 148.0,
166.5.
= 18.3, 21.5, 110.6, 114.2, 119.1, 125.6, 128.4, 129.0,
135.8, 138.3, 139.0, 146.2.
N-(3,5-Dimethylphenyl)morpholine:[43] yellow liquid. IR
(neat) 556, 666, 693, 826, 872, 930, 959, 1016, 1070, 1120,
N-(4-Phenylphenyl)-morpholine:[37] brown solid; mp
30.3__30.6 °C; IR (neat); 632, 693, 719, 762, 826, 864, 922, 1195, 1262, 1303, 1348, 1376, 1449, 1475, 1593, 2818,
1
1054, 1073, 1119, 1178, 1233, 1261, 1305, 1325, 1381,
1448, 1487, 1526, 1604, 2845; 1H NMR (400 MHz,
CDCl3), δ = 3.20 (t, 4H), 3.88 (t, 4H), 6.97 (d, 2H), 7.30 (t,
1H), 7.42 (t, 2H) 7.56 (t, 4H); 13C NMR (100 MHz,
CDCl3) δ = 49.1, 66.9, 115.7, 126.5, 127.8, 128.7, 132.7,
140.7, 150.5.
2851, 2914, 2955, 3013; H NMR (400 MHz, CDCl3), δ =
2.31 (s, 6H), 3.15 (t, 4H), 3.87 (t, 4H), 6.57 (s, 3H); 13C
NMR (100 MHz, CDCl3) δ = 21.6, 49.5, 67.0, 113.7, 122.0,
138.7, 151.4.
2-methyl-N-phenylaniline. pale brown liquid; IR (neat)
692, 761, 878, 1027, 1047, 1077, 1111, 1175, 1250, 1292,
1308, 1418, 1464, 1494, 1593, 3046, 3388; H NMR (400
MHz, CDCl3), δ = 2.25 (s, 3H), 5.37 (br s, 1H), 6.87-7.00
(m, 4H), 7.13 (dt, 1H), 7.18-7.27 (m, 4H); 13C NMR (100
MHz, CDCl3) δ = 17.8, 117.4, 118.8, 120.4, 122.0, 126.7,
128.3, 129.2, 1330.9, 141.2, 144.0.
1
N-Phenyl-4-phenylaniline:[38,39] colorlesshite solid; mp
113.9__114.2 °C (lit.[38] 113 °C); IR (neat) 630, 649, 692,
737, 759, 846, 879, 993, 1004, 1024, 1079, 1115, 1147,
1183, 1262, 1399, 1434, 1484, 1495, 1522, 1595, 3027,
1
3369, 3406; H NMR (400 MHz, CDCl3), δ = 5.79 (br s,
1H), 6.96 (t, 1H), 7.13 (t, 4H), 7.29 (t, 3H), 7.42 (t, 2H),
7.51 (d, 2H), 7.57 (d, 2H); 13C NMR (100 MHz, CDCl3) δ
= 117.8, 118.1, 121.2, 126.5, 126.6, 128.0, 128.7, 129.4,
133.7, 140.8, 142.5, 142.8.
N-Hexyl-1-naphthalenamine:[44] black liquid; IR (neat)
569, 765, 783, 941, 1132, 1251, 1282, 1343, 1375, 1408,
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1477, 1525, 1582, 2854, 2925, 3051; H NMR (400 MHz,
CDCl3), δ = 0.93 (t, 3H), 1.36-1.39(m, 4H), 1.50 (quin,
2H), 1.78 (quin, 2H), 3.27 (t, 2H), 4.31 (br s, 1H), 6.61 (d,
1H), 7.30 (d, 1H), 7.40 (t, 1H), 7.41 (m, 2H), 7.79 (t, 2H);
13C NMR (100 MHz, CDCl3) δ = 14.1, 22.6, 27.0, 29.4,
31.7, 44.2, 104.1, 117.0, 119.7, 123.3, 124.5, 125.6, 126.6,
128.6, 134.3, 143.6.
N-(4-(4-Methoxyphenylamino)phenyl)acetoamide:[40]
[40]
pale brown solid; mp 139.5__139.8 °C (lit.
138__142 °C); IR (neat) 567, 607, 638, 655, 768, 818, 829,
1034, 1106, 1172, 1243, 1296, 1314, 1367, 1440, 1465,
1
1510, 1547, 1592, 1652, 3268, 3419; H NMR (400 MHz),
δ = 2.12 (s, 3H), 3.78 (s, 3H), 5.50 (s, 3H), 6.84 (t, 4H),
7.00 (d, 2H), 7.30 (d, 2H), 7.52 (br s, 1H); 13C NMR (100
MHz, CDCl3) δ =24.2, 55.5, 114.6, 116.4, 121.3, 122.0,
130.2, 136.1, 141.8, 154.9, 168.4. HRMS [DART+]. m/z
calcd for C15H17N2O2: 257.1290 [M+H]+, Found: 257.1295
[M+H]+.
N-Naphthalen-2-yl-morpholine:[31] colorless solid; mp
88.7__89.2 °C (lit. [31] 87__88 °C); IR (neat) 597, 625, 650,
746, 811, 838, 876, 930, 958, 1030, 1046, 1066, 1116,
1148, 1195, 1210, 1254, 1266, 1303, 1354, 1379, 1392,
1446, 1471, 1507, 1595, 1626; 1H NMR (400 MHz,
CDCl3), δ = 3.26 (t, 4H), 3.92 (t, 4H), 7.12 (d, 1H), 7.26
(dd, 1H), 7.31 (t, 1H), 7.41 (t, 1H), 7.70-7.76 (m, 3H). 13C
NMR (100 MHz, CDCl3) δ = 49.7, 66.8, 110.0, 118.8,
123.5, 126.3, 126.7, 127.4, 128.6, 128.7, 134.4, 149.0.
N-4-Hexylamino-acetoamide:[41] pale brown solid; mp
101.2__101.5 °C (lit. [41]108 °C); IR (neat) 571, 604, 709,
731, 749, 820, 899, 924, 963, 1016, 1035, 1091, 1135,
1156, 1178, 1223, 1247, 1278, 1292, 1310, 1364, 1402,
1466, 1481, 1513, 1550, 1600, 1651, 2854, 2929, 2960,
31137, 3293, 3401 ; 1H NMR (400 MHz), δ = 0.90 (t, 3H),
1.31-1.40 (m, 6H), 1.60 (quin, 3H), 2.13 (s, 3H), 3.08 (t,
3H), 3.6 (br s, 1H), 6.56 (d, 2H) 6.97 (s, 1H), 7.25 (d, 2H),
13C NMR (100 MHz, CDCl3) δ = 14.0, 22.6, 24.2, 26.8,
29.4, 31.6, 44.3, 112.9, 122.4, 128..0, 128.1, 145.6, 168.3.
HRMS [DART+]. m/z calcd for C14H23N2O: 235.1810
[M+H]+, Found: 235.1804 [M+H]+.
N-Phenyl-2-naphalenamine:[31]
brown
solid;
mp
105.2__105.5 °C (lit. [31] 107__108 °C); IR (neat) 657, 690,
736, 815, 853, 880, 957, 1017, 1071, 1117, 1172, 1216,
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1239, 1303, 1414, 1464, 1494, 1595, 1626, 3053, 3392; H
NMR (400 MHz, CDCl3), δ = 5.85 (br s, 1H), 7.00 (t, 1H),
7.18 (d, 2H), 7.24 (dd, 1H), 7.31-7.35 (m, 3H), 7.42 (dt,
1H), 7.46 (d, 1H), 7.66 (d, 1H), 7.76 (d, 2H); 13C NMR
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