Polyaniline Nanofiber-Bonded CuI Catalyst
(m, 6 H), 0.90 (t, J = 6.07 Hz, 3 H) ppm. 13C NMR (75 MHz, δ = 155.744, 137.875, 121.487, 116.240, 66.150, 46.493 ppm. GC–
CDCl3, ppm): δ = 147.651, 133.693, 115.638, 111.716, 45.349, MS: m/z = 208 [M]+. C10H12N2O3 (208.22): calcd. C 57.68, H 5.81,
30.043, 29.398, 22.811, 14.398 ppm. MS (EI): m/z = 242 [M +
H]+. C11H16BrN (242.16): calcd. C 54.56, H 6.66, N 5.78; found C
55.06, H 6.55, N 5.82.
N 13.45; found C 57.72, H 5.85, N 14.20.
4-(2-Nitrophenyl)morpholine: (Table 4, entry 11) Yellow solid, iso-
1
lated yield 96%. H NMR (300 MHz, CDCl3): δ = 8.85–8.80 (m,
4-Chloro-N-pentylaniline: (Table 3, entry 11) Yellow oil, isolated
yield 99%. 1H NMR (300 MHz, CDCl3): δ = 7.35 (d, J = 8.31 Hz,
1 H), 8.25–8.10 (m, 1 H), 6.85 (d, J = 7.93 Hz, 2 H), 3.65 (t, J =
5.01 Hz, 2 H), 3.01 (t, J = 5.01 Hz, 2 H) ppm. 13C NMR (75 MHz,
2 H), 6.50 (d, J = 8.31 Hz, 2 H), 4.15 (br. s, 1 H), 3.25–3.15 (m, 2 CDCl3): δ = 139.971, 134.067, 132.512, 122.092, 119.936, 116.532,
H), 1.50–1.25 (m, 6 H), 0.89 (t, J = 6.51 Hz, 3 H) ppm. 13C NMR 67.626, 46.493 ppm. GC–MS: m/z = 208 [M]+. C10H12N2O3
(75 MHz, CDCl3): δ = 147.129, 130.404, 123.627, 115.096, 45.122,
30.486, 29.434, 22.934, 13.917 ppm. MS (EI): m/z = 198 [M +
H]+. C11H16ClN (197.71): calcd. C 66.83, H 8.16, N 7.08; found C
66.86, H 8.15, N 7.12.
(208.22): calcd. C 57.68, H 5.81, N 13.45; found C 57.65, H 5.79,
N 13.50.
4-(4-Bromophenyl)morpholine: (Table 4, entry 12) A white solid,
isolated yield 85%. 1H NMR (300 MHz, CDCl3): δ = 7.49–7.35
(m, 2 H), 6.70–6.50 (m, 2 H), 3.72 (t, J = 5.09 Hz 2 H), 2.98 (t, J
= 5.09 Hz, 2 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 148.234,
133.531, 116.342, 111.798, 67.626, 46.493 ppm. GC–MS: m/z = 242
[M]+. C10H12BrNO (242.11): calcd. C 49.61, H 5.00, N 5.79; found
4-Methoxy-N-pentylaniline: (Table 3, entry 13) Yellow gummy so-
1
lid, isolated yield 99%. H NMR (300 MHz, CDCl3): δ = 8.0 (br.
s, 1 H), 6.80 (d, J = 8.71 Hz, 2 H), 6.60 (d, J = 8.71 Hz, 2 H), 4.40–
3.85 (m, 2 H), 3.70 (s, 3 H), 1.60–1.20 (m, 7 H), 0.88 (t, J = 7.2 Hz,
3 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 150.128, 139.285, C 49.65, H 5.09, N 5.80.
115.312, 114.636, 55.933, 45.104, 31.880, 30.185, 22.958,
1-Phenyl-1H-pyrrole: (Table 4, entry 13) Yellow oil, isolated yield
13.951 ppm. MS (EI): m/z = 194 [M + H]+. C12H19NO (193.29):
1
80%. H NMR (300 MHz, CDCl3 ): δ = 7.42–7.32 (m, 5 H), 6.85
calcd. C 74.57, H 9.91, N 7.25; found C 75.21, H 9.89, N 7.28.
(d, J = 2.55 Hz, 2 H), 6.60 (d, J = 2.55 Hz, 2 H) ppm. 13C NMR
(75 MHz, CDCl3): δ = 139.566, 130.769, 126.926, 123.627, 121.487,
1-Phenylpyrrolidine: (Table 4, entry 3) Yellow oil, isolated yield
67%. 1H NMR (300 MHz, CDCl3): δ = 7.05 (d, J = 8.30 Hz, 2 H), 111.323 ppm. GC–MS: m/z = 144 [M + H]+. C10H9N (143.19):
6.60–6.49 (m, 3 H), 2.75 (d, J = 7.01 Hz, 4 H), 1.85 (d, J = 7.01 Hz, calcd. C 83.88, H 6.34, N 9.78; found C 83.80, H 6.25, N 9.75.
4 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 149.877, 130.577,
1-(4-Bromophenyl)-1H-pyrrole: (Table 4, entry 14) A white solid,
118.523, 113.972, 51.507, 25.429 ppm. MS (EI): m/z = 147 [M]+.
isolated yield 75%, m.p. 94–98 °C. 1H NMR (300 MHz, CDCl3): δ
C10H13N (147.22): calcd. C 81.59, H 8.90, N 9.51; found C 82.07,
= 8.15 (d, J = 7.02 Hz, 2 H), 7.35 (d, J = 7.02 Hz, 2 H), 6.80–6.90
H 8.91, N 9.55.
(m, 2 H), 6.50–6.70 (m, 2 H) ppm. 13C NMR (75 MHz, CDCl3): δ
1-(4-Nitrophenyl)pyrrolidine: (Table 4, entry 4) A pale-yellow solid,
isolated yield 71%. H NMR (300 MHz, CDCl3): δ = 8.20 (d, J =
= 139.416, 133.206, 125.207, 123.627, 119.743, 111.178 ppm. MS
(EI): m/z = 221 [M + H]+. C10H8BrN (222.08): calcd. C 54.08, H
3.63, N 6.31; found C 54.09, H 3.65, N 6.25.
1
8.86 Hz, 2 H), 7.50 (d, J = 8.86 Hz, 2 H), 2.90 (d, J = 7.79 Hz, 4
H), 1.85 (d, J = 7.79 Hz, 4 H) ppm. 13C NMR (75 MHz, CDCl3):
δ = 157.050, 137.807, 121.487, 116.532, 51.507, 25.429 ppm. GC–
MS: m/z = 193 [M + H]+. C10H12N2O2 (192.22): calcd. C 62.49, H
6.29, N 14.57; found C 62.51, H 6.25, N 14.59.
N-Benzylaniline: (Table 5, entry 1) A colorless liquid, isolated yield
1
61%. H NMR (300 MHz, CDCl3): δ = 7.49–7.35 (m, 5 H), 6.85–
6.70 (m, 3 H), 4.50 (d, J = 5.6 Hz, 2 H), 4.00 (br. s, 1 H) ppm. 13C
NMR (75 MHz, CDCl3): δ = 145.796, 140.684, 128.601, 127.732,
126.621, 126.310, 117.949, 114.820, 53.710 ppm. MS (EI): m/z =
183 [M]+. C13H13N (183.25): calcd. C 85.21, H 7.15, N 7.64; found
1-(4-Chlorophenyl)pyrrolidine: (Table 4, entry 5) A white solid, iso-
1
lated yield 82%, m.p. 77–80 °C. H NMR (300 MHz, CDCl3): δ =
7.05 (d, J = 8.75 Hz, 2 H), 6.65 (d, J = 8.75 Hz, 2 H), 3.00 (d, J = C 85.07, H 7.19, N 7.55.
7.02 Hz, 4 H), 1.6 (d, J = 7.02 Hz, 4 H) ppm. 13C NMR (75 MHz,
Benzyl(4-methoxyphenyl)amine: (Table 5, entry 2) A pale-yellow so-
lid, isolated yield 23%, m.p. 48–50 °C. 1H NMR (300 MHz,
CDCl3): δ = 7.35 (d, J = 7.8 Hz, 2 H), 6.85–6.70 (m, 5 H), 6.50 (d,
J = 7.8 Hz, 2 H), 4.20 (d, J = 5.6 Hz, 2 H), 4.0 (br. s, 1 H), 3.75
(s, 3 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 148.234, 141.445,
135.875, 128.425, 126.926, 126.451, 57.028, 56.621 ppm. GC–MS:
m/z = 214 [M + H]+. C14H15NO (213.28): calcd. C 78.84, H 7.09,
CDCl3):
δ = 148.234, 130.577, 123.627, 116.240, 51.507,
25.429 ppm. GC–MS: m/z = 181 [M]+. C10H12ClN (181.66): calcd.
C 66.12, H 6.66, N 7.71; found C 66.19, H 6.65, N 7.70.
1-Phenylpiperidine: (Table 4, entry 7) A pale-yellow thick oil, iso-
lated yield 67%. 1H NMR (300 MHz, CDCl3): δ = 7.05 (d, J =
7.01 Hz, 2 H), 6.70–6.50 (m, 3 H), 3.01 (d, J = 7.01 Hz, 4 H),
1.65–1.51 (m, 6 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 150.239, N 6.57; found C 79.19, H 7.05, N 6.60.
130.644, 118.523, 113.972, 51.507, 26.668, 25.878 ppm. MS (EI):
Benzyl(4-chlorophenyl)amine: (Table 5, entry 4) A light-yellow li-
m/z = 162 [M + H]+. C11H15N (161.25): calcd. C 81.94, H 9.38, N
quid, isolated yield 85%. 1H NMR (300 MHz, CDCl3): δ = 8.10
(br. s, 1 H), 7.41–7.39 (m, 4 H), 6.90–6.80 (d, J = 8.3 Hz, 2 H),
6.65–6.50 (d, J = 8.3 Hz, 2 H), 3.45 (s, 2 H) ppm. 13C NMR
(75 MHz, CDCl3): δ = 144.450, 140.466, 128.445, 127.875, 126.834,
122.532, 116.181, 45.881 ppm. MS (EI): m/z = 218 [M + H]+.
C13H12ClN (206.61): calcd. C 71.72, H 5.56, N 6.43; found C 71.80,
H 5.55, N 6.39.
8.69; found C 81.90, H 9.35, N 8.72.
4-Phenylmorpholine: (Table 4, entry 8) White solid, isolated yield
1
83%, m.p. 52–54 °C. H NMR (300 MHz, CDCl3): δ = 6.85 (d, J
= 7.20 Hz, 2 H), 6.50–6.71 (m, 3 H), 3.63 (t, J = 4.47 Hz, 4 H),
3.17 (t, J = 4.47 Hz, 4 H) ppm. 13C NMR (75 MHz, CDCl3): δ =
151.174, 131.039, 119.302, 113.972, 66.570, 46.493 ppm. GC–MS:
m/z = 164 [M + H]+. C10H13NO (163.22): calcd. C 73.59, H 8.03,
N 8.58; found C 73.62, H 8.05, N 8.61.
N-Cyclohexylaniline: (Table 5, entry 9) A colorless oil, isolated yield
1
98%. H NMR (300 MHz, CDCl3): δ = 8.15–8.10 (m, 2 H), 7.17
4-(4-Nitrophenyl)morpholine: (Table 4, entry 9) Yellow solid, iso-
lated yield 85%. 1H NMR (300 MHz, CDCl3): δ = 8.10 (d, J =
8.01 Hz, 2 H), 6.85 (d, J = 8.01 Hz, 2 H), 3.75 (t, J = 5.02 Hz, 2
H), 3.05 (t, J = 5.02 Hz, 2 H) ppm. 13C NMR (75 MHz, CDCl3):
(t, J = 7.61 Hz, 2 H), 6.67 (t, J = 8.31 Hz, 1 H), 6.57 (d, J =
8.48 Hz, 2 H), 3.31–3.27 (m, 1 H), 2.21–2.07 (m, 2 H), 1.86–1.78
(m, 2 H), 1.51–1.12 (m, 6 H) ppm. 13C NMR [75 MHz, CDCl3/
DMSO (1:3)]: δ = 142.985, 131.061, 116.543, 113.232, 53.017,
Eur. J. Org. Chem. 2010, 3621–3630
© 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
3629