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shis are reported in d units (ppm) relative to CDCl3 (d 77.0). CHar), 7.44–7.26 (m, 6H, CHar), 7.11–7.09 (m, 2H, CHar), 7.08–
Melting points were obtained on a Koer apparatus.
6.90 (m, 4H, CHar), 4.53 (m, 2H), 4.27 (br, 1H, NH), 2.30 (s, 3H),
13C-NMR (75 MHz, CDCl3) d ¼ 20.76, 47.17, 66.74, 120.03,
127.11, 127.16, 129.55, 141.86, 143.8.
General procedure to determine the substrate scope
N-(tert-Butoxycarbonyl)-toluidine (3c). Brow solid obtained
To a stirred solution of tosyl chloride Fmoc chloride, Boc in 98% yield (mp 34–36 ꢀC); 1H-NMR (300 MHz, CDCl3): d ¼
anhydride (2.2 mmol), in H2O (3 mL) was added the N-nucleo- 7.22–7.26 (m, 2H, CHar), 7.08 (d, J ¼ 8.25, 2H, CHar), 6.56 (s, 1H,
phile (2.0 mmol) and conducted in MW. The reaction mixture NH), 2.29 (s, 3H), 1.50 (s, 9H); 13C-NMR (75 MHz, CDCl3): 28.69,
until TLC indicated consumption of the starting material. The 80.64, 119.03, 129.78, 132.87, 136.06, 153.23.
reaction mixture presents a organic precipitate The same,
repeatedly washed with water is subsequently dried.
N-Acetyl-toluidine (3d). Off white to brown ake solid
obtained in 97% yield (mp 34–36 C).
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N-Benzyl-p-toluenesulfonamide (1a). Yellow solid obtained in
N-(p-Nitro-aniline) p-toluenesulfonamide (4a). Yellow ake
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90% yield (mp 115.1–115.9 C); H-NMR (300 MHz, CDCl3): d ¼ solid obtained in 85% yield (mp 190–191 ꢀC). Spectroscopic data
7.76 (d, 2H, J ¼ 8.24, CHar), 7.24–7.32 (m, 4H, CHar), 7.17–7.21, (m, compared to those of the pure product.
2H, CHar), 4.76 (t, 1H, NH, J ¼ 6.15), 4.11 (d, 2H, CH2, J ¼ 6.22),
N-(9-Fluorenylmethoxycarbonyl) p-nitro-aniline (4b). Yellow
2.44 (s, 3H, CH3). 13C-NMR (75 MHz, CDCl3): 21.85, 47.59, 114.34, solid obtained in 80% yield. C; 1H-NMR (300 MHz, CDCl3): d ¼
127.52, 128.20, 129.01, 136.07, 137.26, 136.64, 143.84.
8.14–8.17 (m, 2H, CHar), 7.19–7.79 (m, 10H, CHar), 4.53–4.63
N-(9-Fluorenylmethoxycarbonyl) benzylamine (1b). Colorless (m, 1H, CH), 4.26 (t, 2H, CH2, J ¼ 6.05). 13C-NMR (75 MHz,
solid obtained in 98% yield. 1H-NMR (300 MHz, CDCl3): d ¼ CDCl3): 46.20, 47.32, 66.71, 79.74, 125.00, 127.05, 127.39,
7.58–7.79 (m, 4H, CHar), 7.25–7.46 (m, 5H, CHar), 4.51 (dd, 2H, 127.55, 127.69, 127.27, 128.73, 141.33, 142.42, 143.93, 156.43.
CH2), 4.21–4.39 (m, 2H, CH2). 13C-NMR (75 MHz, CDCl3): 46.20,
N-(tert-Butoxycarbonyl) p-nitro-aniline (4c). Yellow ake oil
47.32, 66.71, 79.74, 125.00, 127.05, 127.39, 127.55, 127.69, obtained in 98% yield. Spectroscopic data compared to those of
127.27, 128.73, 141.33, 142.42, 143.93, 156.43.
the pure product.
N-(tert-Butoxycarbonyl) benzylamine (1c). White solid
N-p-nitro-aniline acetamide (4d). Solid, yellow obtained in
obtained in 98% yield (mp 55–57 ꢀC); 1H-NMR (300 MHz, 96% yield (mp 214–216 ꢀC). Spectroscopic data compared to
CDCl3): d ¼ 7.25–7.35 (m, 5H, CHar), 4.31 (d, J ¼ 5.49, 2H), 1.46 those of the pure product.
(s, 9H) 13C-NMR (75 MHz, CDCl3): 46.20, 47.32, 66.71, 79.74,
125.00, 127.05, 127.39, 127.55, 127.69, 127.27, 128.73, 141.33, obtained in 98% yield (mp 181–183 ꢀC). Spectroscopic data
N-p-Nitro-aniline-p-toluenesulfonamide (5a). White solid
142.42, 143.93, 156.43.
compared to those reported in the literature.20
N-(9-Fluorenylmethoxycarbonyl) p-methoxybenzylamine
N-benzylacetamide (1d). Yellow ake solid obtained in 98%
yield (mp 60–62 C). Spectroscopic data compared to those of (5b). Yellow solid obtained in 95% yield (mp). 1H NMR (300
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the pure product.
MHz, CDCl3) d: 7.77 (d, 2H, J ¼ 7.0 Hz), 7.59 (d, 2H, J ¼ 5.8 Hz),
N-Phenyl-p-toluenesulfonamide (2a). White solid obtained 7.51–7.19 (m, 6H), 6.87 (d, 2H, J ¼ 6.9 Hz), 4.45 (d, 2H, J ¼ 5.5
in 98% yield (mp 101.5–102.2 ꢀC); . 1H-NMR (300 MHz, CDCl3): Hz), 4.45–4.22 (m, 5H) 3.80 (s, 3H). 13C-NMR (75 MHz, CDCl3) d:
7.67 (d, J ¼ 7.5 Hz, 2H, CHar), 7.08–7.32 (m, 5H, H–Ar), 7.11 (d, J 44.6, 47.3, 55.3, 66.6, 114.1, 120.0, 125.0, 127.0, 127.7, 128.9,
¼ 7.5 Hz, 2H, CHar), 2.38 (s, 3H, CH3), 1.74, (s, 1H, NH). 13C- 130.5, 141.3, 143.9, 156.3, 159.1.
NMR (75 MHz, CDCl3): 21.5, 111.1, 121.1, 125.7, 126.0,
129.5136.7, 143.1. 149.6.
N-(tert-Butoxycarbonyl) p-methoxybenzylamine (5c). Col-
ourless oil 98. 1H-NMR (300 MHz, CDCl3) d ¼ 7.26–7.19 (m, 2H,
N-(9-Fluorenylmethoxycarbonyl) aniline (2b). Brown solid CHar), 6.87–6.84 (m, 2H, CHar), 4.25–4.23 (m, 2H, CH2), 3.79 (s,
obtained in 92% yield; H-NMR (300 MHz, CDCl3) d ¼ 7.79 (d, 3H), 1.47 (s, 9H), 13C-NMR (75 MHz, CDCl3): 28.76, 44.52, 55.64,
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2H, CHar, J ¼ 7.4 Hz), 7.63 (d, 2H, CHar, J ¼ 7.0 Hz), 7.43–7.05 79.74, 114.34, 129.19, 131.36, 156.18, 159.25.
(m, 8H, CHar), 6.63 (br s, 1H), 4.56 (d, 2H, J ¼ 6.4 Hz), 4.28 (t,
p-Methoxybenzyl acetamide (5d). Yellow oil obtained in 97%
1H, J ¼ 6.4 Hz). 13C-NMR (75 MHz, CDCl3) d: 47.1, 66.8, 118.81, yield. Spectroscopic data compared to those of the pure
120.0, 123.6, 124.9, 127.1, 127.8, 129.1, 137.7, 141.4143.8, 153.4. product.
N-(tert-Butoxycarbonyl) aniline (2c). White solid obtained in
N-Octyl p-toluenesulfonamide (6a). Yellow oil obtained in
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94% yield (mp 133–137 ꢀC); 1H-NMR (300 MHz, CDCl3) 1H-NMR 83% yield. H-NMR (300 MHz, CDCl3) d ¼ 7.73 (d, J ¼ 7.4 Hz,
(300 MHz, CDCl3): d ¼ 7.38–7.25 (m, 4H), 1.52 (s, 9H), 7.25 (t, 2H, CHar), 7.31 (d, J ¼ 7.4 Hz, 2H, CHar), 3.17–3.15 (m, 2H,
1H, Ar, J ¼ 7.27; J ¼ 1.38), 6.49 (s, 1H, NH), 13C-NMR (75 MHz, NCH2), 2.40 (s, 3H, CH3), 1.56–1.53 (m, 2H, CH2), 1.37–1.20 (m,
CDCl3): 28.69, 80.83, 118.89, 123.38, 129.31, 138.69, 153.99.
10H, 5 CH2), 0.90–1.00 (m, 3H, CH3), 13C-NMR (75 MHz, CDCl3):
N-Acetyl aniline (2d). White solid obtained in 98% yield (114– 14.38, 22.83, 24.53, 43.53, 27.11, 29.48, 29.61, 31.23, 41.50,
116 ꢀC). Spectroscopic data compared to those of the pure product. 127.28, 128.97, 136.37, 141.74.
N-Toluidine p-toluenesulfonamide (3a). Coloress oil
obtained in 98% yield. Spectroscopic data compared to those of solid obtained in 95% yield (mp 91–93 ꢀC). 1H-NMR (300 MHz,
the pure product.
N-(9-Fluorenylmethoxycarbonyl) octylamine (6b). Pale yellow
CDCl3): d ¼ 7.80–7.19 (m, 8H, CHar), 4.50–4.32 (m, 2H, CH2O),
N-(9-Fluorenylmethoxycarbonyl)-toluidine (3b). Colorless 4.32–4.20 (m, 1H, CH), 3.19 (dd, 2H, NCH2, J ¼ 12.9, J ¼ 6.66),
solid obtained in 90% yield (mp 195–197 ꢀC). 1H-NMR (300 1.58–1.40 (m, 2H, CH2), 1.38–1.05 (m, 10H, 5 CH2), 0.90–0.70
MHz, CDCl3) d ¼ 7.79–7.77 (m, 2H, CHar), 7.63–7.61 (m, 2H, (m, 3H, CH3). 13C-NMR (75 MHz, CDCl3): 14.42, 22.97, 44.52,
18756 | RSC Adv., 2015, 5, 18751–18760
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