JOURNAL OF CHEMICAL RESEARCH 2013 379
2-(4-Bromobenzyl)-1H-perimidine (7b): M.p. 170–172 °C, 1H
NMR (200 MHz, DMSO-d6) δ 3.54 (s, 2H), 6.36 (d, J = 7.2, 1H),
6.94–7.07 (m, 4H), 7.33 (d, J = 8.2 Hz, 2H), 7.53 (d, J = 8.2, 2H),
10.61 (s, 1H); 13C NMR (50 MHz, DMSO-d6) δ 38.98–41.41 (DMSO-
d6 + CH2), 112.64, 118.21, 121.10, 124.07, 129.12, 129.31, 131.72,
132.01, 135.72, 136.96, 156.41. Anal. Calcd for C18H13BrN2: C, 64.11;
H, 3.89; N, 8.31. Found: C, 64.10; H, 3.87; N, 8.30%. ESI-MS: 337.21
[M]+.
2-(3,4,5-Trimethoxybenzyl)-1H-perimidine (14b): M.p. 135–136 °C,
1H NMR (200 MHz, DMSO-d6) δ 3.50 (s, 2H), 3.61 (s, 3H), 3.75 (s,
6H), 6.44 (d, J = 7.0 Hz, 2H), 6.72 (s, 2H), 7.05 (t, J = 7.4, 2H), 7.11
(d, J = 7.0, 2H). 13C NMR (50 MHz, DMSO-d6) δ 40.72, 55.81, 59.84,
106.11, 118.62, 121.06, 128.34, 131.76, 134.82, 136.33, 152.71,
156.24. Anal. Calcd for C21H20N2O3: C, 72.40; H, 5.79; N, 8.04.
Found: C, 72.44; H, 5.85; N, 8.01%. ESI-MS: 349.42 [M+1]+.
2-(3-Methylbenzyl)-1H-perimidine (8b): M.p. 175–176 °C, 1H
NMR (200 MHz, DMSO-d6) δ 2.28 (s, 3H), 3.51 (s, 2H), 6.26 (dd,
J = 6.2 Hz, 1H), 6.53 (dd, J = 6.6 Hz, 1H), 6.96–7.19 (m, 5H), 7.22 (s,
3H), 10.58 (s, 1H); 13C NMR (50 MHz, DMSO-d6) δ 21.70, 41.74,
102.53, 113.91, 118.22, 119.50, 122.05, 126.52, 128.13, 128.61,
129.14, 129.66, 130.07, 135.81, 137.43, 138.22, 156.71. Anal. Calcd
for C19H16N2: C, 83.79; H, 5.92; N, 10.29. Found: C, 83.80; H, 5.90;
N, 10.30%. ESI-MS: 273.36 [M+1]+.
Received 7 March 2013; accepted 12 April 2013
Published online: 12 June 2013
References
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2-(2-Chlorobenzyl)-1H-perimidine (9b): M.p. 180–182 °C, 1H
NMR (200 MHz, DMSO-d6) δ 3.72 (s, 2H), 6.25 (dd, J = 6.6, 1H),
6.41 (dd, J = 6.6, 1H), 6.95–7.07 (m, 4H), 7.30–7.7.32 (m, 2H), 7.45
(m, 2H), 10.69 (s, 1H); 13C NMR (50 MHz, DMSO-d6) δ 56.72,
117.33, 117.60, 119.41, 119.66, 122.63, 125.87, 129.13, 129.8,
130.14, 135.80, 157.11. Anal. Calcd for C18H13ClN2: C, 73.85; H,
4.48; N, 9.57. Found: C, 73.86; H, 4.53; N, 9.61%. ESI-MS: 293.79
[M+1]+.
4
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8
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2-(3-Chlorobenzyl)-1H-perimidine (10b): M.p. 175–176 °C (lit.26
10 J. Taylor and J. Russell, U. S. Patent 3,956,497, 1975.
11 J. Taylor and J. Russell, J. U. S. Patent 3,956,496, 1974.
12 A.F. Pozharskii, I.V. Komissarov, I.T. Filippov, A.A. Konstantinchenko,
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1
171–173 °C), H NMR (200 MHz, DMSO-d6) δ 3.60 (s, 2H), 6.34–
7.46 (m, 10H), 10.64 (s, 1H). Anal. Calcd for C18H13ClN2: C, 73.85; H,
4.48; N, 9.57. Found: C, 73.82; H, 4.45; N, 9.55%. ESI-MS: 293.76
[M+1]+.
2-(4-Chlorobenzyl)-1H-perimidine (11b): M.p. 183–185 °C (lit.26
1
183–185 °C), H NMR (200 MHz, DMSO-d6) δ 3.58 (s, 2H), 6.30–
7.42 (m, 10H), 10.62 (s, 1H). Anal. Calcd for C18H13ClN2: C, 73.85; H,
4.48; N, 9.57. Found: C, 73.84; H, 4.46; N, 9.56%. ESI-MS: 293.7
[M+1]+.
2-(2,6-Dichlorobenzyl)-1H-perimidine (12b): M.p. 194–195 °C, 1H
NMR (200 MHz, DMSO-d6) δ 3.93 (s, 2H), 6.30 (dd, J = 1.2, 2H),
6.93–7.10 (m, 4H), 7.30–7.35 (m, 1H), 7.48 (d, J = 1.6, 1H), 10.76 (s,
1H); 13C NMR (50 MHz, DMSO-d6) δ 38.45, 119.18, 121.98, 128.89,
129.04, 130.17, 132.91, 135.67, 136.32, 154.83. Anal. Calcd for
C18H12Cl2N2: C, 66.07; H, 3.70; N, 8.56. Found: C, 66.10; H, 3.75; N,
8.60%. ESI-MS: 327.2 [M]+, 329.2 [M+2]+.
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2-[(4-Chlorophenoxy)methyl]-1H-perimidine (13b): M.p. 175–
176 °C, 1H NMR (200 MHz, DMSO-d6) δ 4.72 (s, 2H), 6.47 (m, 2H),
7.11 (s, 6H), 7.42 (m, 2H), 10.73 (s, 1H); 13C NMR (50 MHz, DMSO-
d6) δ 56.72, 117.33, 117.61, 122.60, 125.82, 129.13, 129.83, 130.06,
135.78, 153.67, 157.32. Anal. Calcd for C17H11ClN2O: C, 69.28; H,
3.76; N, 9.50. Found: C, 69.32; H, 3.80; N, 9.54%. ESI-MS: 309.81
[M+1]+.
2145.
26 J. She, Z. Jiang and Y. Wang, Synlett, 2009, 2023.