B. T. Cho, S. K. Kang / Tetrahedron 61 (2005) 5725–5734
5733
143.6, 148.2. Calcd for C11H11NS: C, 69.80; H, 5.86; N,
7.40; S, 16.94. Found: C, 69.84; H, 5.95; N, 7.21; S, 16.82.
2H, JZ8.53 Hz), 6.63 (t, 1H, JZ7.30 Hz), 7.05 (t, 2H, JZ
7.84 Hz), 7.09–7.30 (m, 4H); 13C NMR (75 MHz, CDCl3) d
25.6, 53.4, 113.6, 117.8, 127.5, 129.1, 129.4, 132.6, 144.1,
147.2. Calcd for C14H14NCl: C, 72.57; H, 6.09; N, 6.04.
Found: C, 72.55; H, 6.05; N, 6.12.
4.4.5. N-Phenyl-(20-pyridinemethyl)amine (30). Oil; 99%
yield using boric or p-toluenesulfonc acid as activator; IR
(neat, cmK1) 3416, 3028, 2972, 2843, 2788, 1566, 1542,
1028, 737, 700; 1H NMR (300 MHz, CDCl3) d 4.45 (s, 3H),
6.65 (d, 2H, JZ7.63 Hz), 6.71 (t, 1H, JZ7.33 Hz), 7.13–
7.20 (m, 3H), 7.32 (d, 1H, JZ7.63 Hz), 7.62 (td, 1H, JZ
1.53, 7.11 Hz), 8.57 (d, 1H, JZ4.27 Hz); 13C NMR
(75 MHz, CDCl3) d 49.8, 1137, 118.2, 122.2, 122.7,
129.8, 137.3, 148.5, 149.7, 159.2. Calcd for C12H12N2: C,
78.23; H, 6.57; N, 15.21. Found: C, 78.27; H, 6.67; N, 15.32.
4.4.11. N-(p-Chlorophenyl)-1-phenylethylamine (36). Mp
59–60 8C; 99% yield using p-toluenesulfonic acid as
activator; IR (KBr, cmK1) 3432, 2997, 2866, 1596, 1496;
1H NMR (300 MHz, CDCl3) d 1.48 (d, 3H, JZ6.88 Hz),
4.03 (br s, 1H), 4.40 (q, 1H, JZ6.69 Hz), 6.38 (d, 2H, JZ
8.80 Hz), 6.99 (d, 2H, JZ9.08 Hz), 7.17–7.36 (m, 5H); 13C
NMR (75 MHz, CDCl3) d 25.5, 53.9, 114.6, 122.0, 126.0,
127.3, 128.9, 129.1, 144.9, 145.9. Calcd for C14H14NCl: C,
72.57; H, 6.09; N, 6.04. Found: C, 72.52; H, 6.12; N, 6.09.
4.4.6. N-Phenyl-1-phenylethylamine (31). Oil; 99% yield
using boric acid as activator; IR (neat, cmK1) 3411, 3055,
2926, 1602, 1503; H NMR (300 MHz, CDCl3) d 1.47 (d,
1
4.4.12. N-Phenyl-1-phenylpropylamine (37). Oil; 99%
3H, JZ6.88 Hz), 3.99 (br s, 1H), 4.44 (q, 1H, JZ6.69 Hz),
6.46 (d, 2H, JZ7.43 Hz), 6.61 (t, 1H, JZ7.29 Hz), 7.05 (dd,
2H, JZ8.53, 7.43 Hz), 7.17 (m, 1H), 7.2–7.34 (m, 4H); 13C
NMR (75 MHz, CDCl3) d 25.6, 53.8, 113.6, 117.5, 126.1,
127.2, 128.9, 129.4, 145.5, 147.5. Calcd for C14H15N: C,
85.24; H, 7.66; N, 7.10. Found: C, 85.27; H, 7.73; N, 7.08.
yield using boric acid as activator; IR (neat, cmK1) 3411,
3025, 2963, 2930, 1604, 1509, 1318, 747, 701; H NMR
1
(200 MHz, CDCl3) d 0.94 (t, 3H, JZ7.33 Hz), 1.81 (quintet,
2H, JZ7.10 Hz), 4.04 (br s, 1H), 4.21 (t, 2H, JZ6.72 Hz),
6.50 (d, 2H, JZ7.63 Hz), 6.02 (t, 1H, JZ7.33 Hz), 7.07 (t,
2H, JZ7.94 Hz), 7.16–7.35 (m, 5H); 13C NMR (50 MHz,
CDCl3) d 11.4, 32.3, 60.4, 113.9, 117.8, 127.2, 127.5, 129.2,
129.8, 144.6, 148.2. Calcd for C15H17N: C, 85.26; H, 8.11;
N, 6.63. Found: C, 85.29; H, 8.17; N, 6.72.
4.4.7. N-Phenyl-1-(o-tolyl)ethylamine (32). Oil; 99% yield
using boric acid as activator; IR (neat, cmK1) 3411, 3050,
3016, 2967, 2925, 2867, 1601, 1504, 1318, 749, 691; H
1
NMR (300 MHz, CDCl3) d 1.45 (d, 3H, JZ6.72 Hz), 2.42
(s, 3H), 3.97 (br s, 1H), 4.65 (q, 1H, JZ6.61 Hz), 6.43 (d,
2H, JZ8.24 Hz), 6.62 (t, 1H, JZ6.72 Hz), 7.03–7.18 (m,
5H), 7.40 (m, 1H); 13C NMR (75 MHz, CDCl3) d 19.6, 23.6,
50.5, 113.7, 117.8, 125.4, 127.3, 129.8, 131.3, 135.2, 143.4,
148.0. Calcd for C15H17N: C, 85.26; H, 8.11; N, 6.63.
Found: C, 85.27; H, 8.14; N, 6.56.
4.4.13. 2,3,3-Trimethylindoline (38). Oil; 99% yield using
benzoic or p-toluenesulfonic acid as activator; IR (neat,
cmK1) 3362, 2960, 2861, 1612, 1467, 1378, 1248, 1164,
1
748; H NMR (300 MHz, CDCl3) d 1.03 (s, 3H), 1.16 (d,
3H, JZ6.33 Hz), 1.27 (s, 3H), 3.48 (q, 1H, JZ6.51 Hz),
3.64 (br s, 1H), 6.58 (d, 1H, JZ7.70 Hz), 6.71 (m, 1H),
6.95–7.01 (m, 2H); 13C NMR (75 MHz, CDCl3) d 15.6,
22.8, 26.6, 43.7, 65.5, 109.6, 119.1, 122.5, 127.4, 139.3,
149.5. Calcd for C11H15N: C, 81.94; H, 9.38; N, 8.69.
Found: C, 81.82; H, 9.31; N, 8.54.
4.4.8. N-Phenyl-1-(p-tolyl)ethylamine (33). Oil; 99% yield
using boric acid as activator; IR (neat, cmK1) 3407, 3047,
2964, 2919, 2868, 1602, 1505, 1322, 750, 693; H NMR
1
4.4.14. 1-Methoxy-2-(20-ethyl-60-methylanilino)propane
(metolachlor base) (48). Rf 0.62 (EtOAc/hexane 1:2); oil;
(300 MHz, CDCl3) d 1.45 (d, 3H, JZ6.60 Hz), 2.28 (s, 3H),
3.79 (br s, 1H), 4.40 (q, 1H, JZ6.69 Hz), 6.46 (d, 2H, JZ
7.70 Hz), 6.59 (t, 1H, JZ7.29 Hz), 7.01–7.11 (m, 4H), 7.20
(d, 2H, JZ7.98 Hz); 13C NMR (75 MHz, CDCl3) d 21.6,
25.6, 53.6, 113.6, 117.5, 126.1, 129.4, 129.7, 136.7, 142.5,
147.6. Calcd for C15H17N: C, 85.26; H, 8.11; N, 6.63.
Found: C, 85.31; H, 8.12; N, 6.67.
99% yield using boric acid as activator; IR (neat, cmK1
)
1
3382, 2964, 2929, 2873, 1593, 1462, 1256, 1105, 756; H
NMR (300 MHz, CDCl3) d 1.17 (d, 3H, JZ6.60 Hz), 1.22
(t, 3H, JZ7.43 Hz), 2.27 (s, 3H), 2.63 (q, 2H, JZ7.61 Hz),
3.31 (d, 2H, JZ1.38 Hz), 3.33 (m, 1H), 3.35 (s, 3H), 6.84 (t,
1H, JZ7.43 Hz), 6.95–7.01 (m, 2H); 13C NMR (75 MHz,
CDCl3) d 15.0, 18.9, 19.4, 24.6, 53.2, 59.4, 76.5, 121.9,
126.7, 128.9, 130.0, 135.7, 144.5. Calcd for C13H21NO: C,
75.32; H, 10.21; N, 6.76. Found: C, 75.26; H, 10.17; N, 6.80.
4.4.9. N-Phenyl-1-(p-methoxyphenyl)ethylamine (34).
Oil; 99% yield using boric acid as activator; IR (neat,
cmK1) 3401, 2962, 2833, 1609, 1504, 1238, 1179, 1035,
1
831, 751, 695; H NMR (300 MHz, CDCl3) d 1.46 (d, 3H,
JZ6.88 Hz), 3.74 (s, 3H), 3.82 (s, 1H), 4.41 (q, 1H, JZ
6.69 Hz), 6.48 (dd, 2H, JZ8.67, 0.93 Hz), 6.61 (t, 1H, JZ
7.29 Hz), 6.82 (d, 2H, JZ8.80 Hz), 7.06 (dd, 2H, JZ7.43,
8.53 Hz), 7.24 (d, 2H, JZ8.80 Hz); 13C NMR (75 MHz,
CDCl3) d 25.5, 53.2, 55.6, 113.5, 114.2, 117.4, 127.1, 129.3,
137.5, 147.5, 158.6. Calcd for C15H17NO: C, 79.26; H, 7.54;
N, 6.16. Found: C, 79.32; H, 7.62; N, 6.34.
4.4.15. N-(trans-Cinnamyl)-1-naphthylmethylamine
(naftifine base) (49). Rf 0.08 (EtOAc/hexane 1:2);
39–40 8C (lit.28 39.5–40.5 8C); 78% yield using benzoic
acid as activator; IR (KBr, cmK1) 3314, 3057, 3025, 2920,
2817, 1597, 1494, 1447, 967, 779, 692; 1H NMR (300 MHz,
CDCl3) d 1.88 (br s, 1H), 3.50 (dd, 2H, JZ6.33, 1.10 Hz),
4.24 (s, 2H), 6.33 (dt, 1H, JZ15.68, 6.26 Hz), 6.54 (d, 1H,
JZ15.95 Hz), 7.15–7.53 (m, 9H), 7.74 (d, 1H, JZ7.98 Hz),
7.83 (d, 1H, JZ7.70 Hz), 8.08 (d, 1H, JZ7.98 Hz); 13C
NMR (75 MHz, CDCl3) d 51.2, 52.1, 123.9, 125.9, 125.7,
126.0, 126.4, 126.5, 126.6, 127.7, 128.1, 128.5, 129.0,
131.9, 132.0, 135.9, 137.3. Calcd for C20H19N: C, 87.87; H,
7.01; N, 5.12. Found: C, 87.89; H, 7.02; N, 5.15.
4.4.10. N-Phenyl-1-(p-chlorophenyl)ethylamine (35). Oil;
)
99% yield using boric acid as activator; IR (neat, cmK1
3408, 3050, 2965, 2924, 2866, 1604, 1506, 1322, 1013, 755,
696; 1H NMR (300 MHz, CDCl3) d 1.43 (d, 3H, JZ
6.88 Hz), 3.83 (br s, 1H), 4.39 (q, 1H, JZ6.69 Hz), 6.43 (d,