Synthesis and Algicidal Activity of New Dichlorobenzylamine Derivatives against Harmful Red Tides
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similar to that described for 1 (93.4% yield): H NMR δ 3.74 (s, 2H), δ 2.63 (t, 2H), δ 1.70 (m, J = 6.9 Hz, 1H),
(300 MHz, CDCl ) δ 7.43 (d, J = 2.1 Hz, 1H), δ 7.39 (d, δ 1.42 (m, J = 6.9 Hz, 2H), δ 1.28 (b, 1H), δ 0.90 (d, 6H).
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J = 8.0 Hz, 1H), δ 7.17 (dd, J = 8.0 and 2.1 Hz, 1H), δ 3.74
(s, 2H), δ 2.62 (t, J = 6.9 and 7.3 Hz, 2H), δ 1.53 (m, J = 2.1.10. 3,4-Dichlorobenzyl-(2-methoxyethyl)amine (10)
6.9 Hz, 4H), δ 1.25 (b, 1H), δ 0.93 (t, J = 7.32 Hz, 3H). Compound 10 was prepared as a colorless liquid in a
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manner similar to that described for 1 (92.1% yield): H
2.1.4. (3,4-Dichlorobenzyl)pentylamine (4)
NMR (300 MHz, CDCl ) δ 7.45 (d, J = 1.8 Hz, 1H), δ
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Compound 4 was prepared as a colorless liquid in a 7.39 (d, J = 8.0 Hz, 1H), δ 7.18 (dd, J = 8.0 and 1.8 Hz,
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manner similar to that described for 1 (68.2% yield): H 1H), δ 3.76 (s, 2H), δ 3.52 (t, J = 5.1 Hz, 2H), δ 3.35 (s,
NMR (300 MHz, CDCl ) δ 7.44 (d, J = 1.83 Hz, 1H), δ 3H), δ 2.79 (t, J = 5.3 Hz, 2H).
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7.39 (d, J = 8.43 Hz, 1H), δ 7.18 (dd, J = 1.83 and 8.43 Hz,
1H), δ 3.74 (s, 2H), δ 2.61 (t, J = 7.32 Hz, 2H), δ 1.55 (m, 2.1.11. 3,4-Dichlorobenzyl-(3-methoxypropyl)-mine (11)
J = 6.96 Hz, 2H), δ 1.32 (m, 4H), δ 0.91 (t, J = 6.96 Hz, 3H). Compound 11 was prepared as a colorless liquid in a
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manner similar to that described for 1 (94% yield): H
2.1.5. (3,4-Dichlorobenzyl)hexylamine (5)
NMR (300 MHz, CDCl ) δ 7.43 (d, J = 1.83 Hz, 1H), δ 7.39
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Compound 5 was prepared as a colorless liquid in a (d, J = 8.04 Hz, 1H), δ 7.17 (dd, J = 8.04 and 1.83 Hz,
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manner similar to that described for 1 (88% yield): H 1H), δ 3.74 (s, 2H), δ 3.47 (t, J = 6.21 Hz, 2H), δ 3.33 (s
NMR (300 MHz, CDCl ) δ 7.43 (d, J = 2.19 Hz, 1H), δ 3H), δ 2.71 (t, J = 6.21 Hz, 2H), δ 1.81 (m, J = 6.21, 2H).
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7.39 (d, J = 8.43 Hz, 1H), δ 7.17 (dd, J = 8.43 and 2.19 Hz,
1H), δ 3.74 (s, 2H), δ 2.61 (t, J = 7.32 and 6.96 Hz, 2H), 2.1.12. 3,4-Dichlorobenzyl-(2,2-dimethoxyethyl)amine (12)
δ 1.51 (m, 8H), δ 0.90 (t, J = 6.96 Hz, 3H).
Compound 12 was prepared as a colorless liquid in a
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manner similar to that described for 1 (88.3% yield): H
2.1.6. (3,4-Dichlorobenzyl)pentylamine (6)
NMR (300 MHz, CDCl ) δ 7.44 (d, J = 1.8 Hz, 1H), δ
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Compound 6 was prepared as a colorless liquid in a 7.39 (d, J = 8.0 Hz, 1H), δ 7.17 (dd, J = 8.0 and 1.8 Hz,
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manner similar to that described for 1 (83% yield): H 1H), δ 4.48 (t, J = 5.5 Hz, 1H), δ 3.76 (s, 2H), δ 3.38 (s,
NMR (300 MHz, CDCl ) δ 7.43 (d, J = 2.22 Hz, 1H), δ 6H), δ 2.73 (d, J = 5.5 Hz, 2H).
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7.39 (d, J = 8.43 Hz, 1H), δ 7.17 (dd, J = 8.43 and 2.22 Hz,
1H), δ 3.73 (s, 2H), δ 2.61 (t, J = 6.96 and 7.32 Hz, 2H), 2.1.13. 3,4-Dichlorobenzyl-(4,4-dimethoxybutyl)amine (13)
δ 1.51 (m, 10H), δ 0.90 (t, J = 6.96 Hz, 3H).
Compound 13 was prepared as a colorless liquid in a
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manner similar to that described for 1 (87.5% yield): H
2.1.7. (3,4-Dichlorobenzyl)isobutylamine (7)
NMR (300 MHz, CDCl ) δ 7.43 (d, J = 1.8 Hz, 1H), δ
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Compound 7 was prepared as a colorless liquid in a 7.39 (d, J = 8.0 Hz, 1H), δ 7.17 (dd, J = 8.0 and 1.8 Hz,
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manner similar to that described for 1 (90% yield): H 1H), δ 4.38 (t, J = 5.49 Hz, 1H), δ 3.74 (s, 2H), δ 3.31 (s,
NMR (300 MHz, CDCl ) δ (d, J = 1.83 Hz, 1H), δ 7.39 (d, 6H), δ 2.64 (t, 2H), δ 1.69 (m, 4H).
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J = 8.07 Hz, 1H), δ 7.18 (dd, J = 1.83 and 8.07 Hz, 1H),
δ (d, J = Hz, 1H), δ 3.78 (s, 2H), δ 2.41 (d, J = 6.96 Hz, 2.1.14. N'-(3,4-Dichlorobenzyl)-N,N-dimethylethane-1,2-
2H), δ 1.79 (m, 1H), δ 0.92 (d, J = 6.6 Hz, 6H).
diamine (14)
Compound 14 was prepared as a colorless liquid in a
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manner similar to that described for 1 (93.2% yield): H
2.1.8. sec-Butyl-(3,4-dichlorobenzyl)amine (8)
Compound 8 was prepared as a colorless liquid in a NMR (300 MHz, CDCl ) δ 7.44 (d, J = 2.2 Hz, 1H), δ
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manner similar to that described for 1 (91% yield): H 7.39 (d, J = 8.4 Hz, 1H), δ 7.18 (dd, J = 8.4 and 2.2 Hz,
NMR (300 MHz, CDCl ) δ 7.44 (d, J = 1.47 Hz, 1H), δ 7.38 1H), δ 3.76 (s, 2H), δ 2.68 (m, J = 5.8 Hz, 2H), δ 2.45 (t,
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(d, J = 8.07 Hz, 1H), δ 7.18 (dd, J = 8.07 and 1.47 Hz, J = 5.8 Hz, 2H), δ 2.21 (s, 6H), δ 2.12 (s, 1H).
1H), δ 3.79 (m, J = 13.56, 10.23 Hz, 2H), δ 2.63 (m, J =
6.24 Hz, 1H), δ 1.57 (m, 1H), δ 1.06 (d, 3H), δ 0.92 (t, 3H). 2.1.15. N'-(3,4-Dichlorobenzyl)-N,N-diethylethane-1,2-
diamine (15)
2.1.9. 3,4-Dichlorobenzyl-(3-methylbutyl)amine (9)
Compound 15 was prepared as a colorless liquid in a
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Compound 9 was prepared as a colorless liquid in a manner similar to that described for 1 (89.5% yield): H
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manner similar to that described for 1 (94% yield): H NMR (300 MHz, CDCl ) δ 7.44 (d, J = 1.8 Hz, 1H), δ 7.39
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NMR (300 MHz, CDCl ) δ 7.43 (d, J = 2.19 Hz, 1H), δ 7.38 (d, J = 8.0 Hz, 1H), δ 7.18 (dd, J = 8.0 and 1.8 Hz, 1H),
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(d, J = 8.0 Hz, 1H), δ 7.17 (dd, J = 8.0 and 2.19 Hz, 1H), δ 3.76 (s, 1H), δ 2.68 (m, 8H), δ 1.06 (t, J = 6.9 Hz, 6H).