heated at 175–178°C on a glycerin bath for 2–4 h. The course of the reaction was monitored using TLC. The mixture was
dissolved in CHCl , extracted with HCl (3%) and NaOH (2%), washed with distilled H O until neutral, and evaporated. The
3
2
solid was worked up with Me CO. The resulting precipitate was filtered off.
2
α-Benzoylamino-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide (3a), C
H N O , was prepared from
19 22 2 4
homoveratrylamine (0.4 g, 2.2 mmol) and 2-benzamidoethanoic acid (0.4 g, 2.23 mmol). Yield 88% (0.66 g), mp 92–94°Ñ
–1
(Me CO), R 0.64. IR spectrum (ν, cm ): 3323, 3297 (NH), 3075, 2932, 2835 (Ar-CH), 1672, 1633 (N-C=O), 1547, 1517.
2
f
1
Í NMR spectrum (400 MHz, ÑDCl , δ, ppm, J/Hz): 2.71 (2Í, t, J = 7.1, Í-α), 3.46 (2Í, q, J = 7, Í-β), 3.7 (3Í, s, ÎÑÍ ),
3
3
3.76 (3Í, s, ÎÑÍ ), 4.01 (2Í, d, J = 5.1, Í-2′), 6.56 (1Í, t, J = 5.7, NH-β), 6.62–6.67 (3Í, m, Ar-2, 5, 6), 7.21 (1Í, t, J = 4.7,
3
1
NH-8′′), 7.37 (2Í, t, J = 7.7, Í-3′′, 5′′), 7.46 (1Í, tt, J = 2.2, 7.5, Í-4′′), 7.74 (2Í, dd, J = 1.4, 7.0, Í-2′′, 6′′). Í NMR spectrum
(400 MHz, ÑD ÎD, δ, ppm, J/Hz): 2.67 (2Í, t, J = 7.3, Í-α), 3.36 (2Í, t, J = 7.4, Í-β), 3.69 (3Í, s, ÎÑÍ ), 3.74 (3Í, s,
3
3
ÎÑÍ ), 3.92 (2Í, s, Í-2′), 6.67 (1Í, dd, J = 1.9, 8.1, H-6), 6.73 (1Í, d, J = 8.1, H-5), 6.77 (1Í, d, J = 1.9, H-2), 7.41 (2Í, t,
3
13
J = 7.7, Í-3′′, 5′′), 7.49 (1Í, tt, J = 2.1, 7.8, Í-4′′), 7.80 (2Í, dd, J = 1.4, 7.7, Í-2′′, 6′′). C NMR spectrum (100 MHz, ÑDCl ,
3
δ, ppm): 35.35 (Ñ-α), 41.08 (Ñ-β), 44.03 (Ñ-2′), 55.00 (ÎÑÍ ), 56.03 (ÎÑÍ ), 111.42 (Ñ-2), 111.96 (Ñ-5), 120.83 (Ñ-6),
3
3
127.31 (Ñ-2′′, 6′′), 128.82 (Ñ-3′′, 5′′), 131.22 (Ñ-4), 132.13 (Ñ-4′′), 133.56 (Ñ-1′′), 147.84 (Ñ-4), 149.17 (Ñ-4), 167.96, 169.17
(Ñ=Î).
α-Benzoylamino-N-[2-(3,4-dimethoxyphenyl)ethyl]propionamide (3b), C
H N O , was prepared from
20 24 2 4
homoveratrylamine (0.5 g, 2.76 mmol) and 2-benzamidopropanoic acid (0.54 g, 2.8 mmol). Yield 71.5% (0.703 g),
–1
mp 121–123°Ñ (Me CO), R 0.69. IR spectrum (ν, cm ): 3417, 3317 (NH), 3070, 2931, 2834 (Ar-CH), 1662, 1634 (N-C=O),
2
f
1
1547, 1519. Í NMR spectrum (400 MHz, ÑDCl , δ, ppm, J/Hz): 1.39 (3Í, d, J = 6.9, Í-3′), 2.70 (2Í, t, J = 7.1, Í-α), 3.44
3
(2Í, m, Í-β), 3.74 (3Í, s, ÎÑÍ ), 3.76 (3Í, s, ÎÑÍ ), 4.62 (1Í, td, J = 1.7, 7.2, Í-2′), 6.61 (1Í, d, J = 1.7, Í-2), 6.63 (1Í,
3
3
dd, J = 1.8, 7.9, Í-6), 6.65 (1Í, d, J = 8, Í-5), 6.66 (1Í, br.s, NH-β), 6.96 (1Í, d, J = 7.3, NH-8′′), 7.36 (2Í, t, J = 8.2, Í-3′′,
5′′), 7.45 (1Í, tt, J = 2, 7.5, Í-4′′), 7.71 (2Í, dt, J = 1.4, 8.2, Í-2′′, 6′′).
α-Benzoylamino-N-[2-(3,4-dimethoxyphenyl)ethyl]butyramide (3c), C
H N O , was prepared from
21 26 2 4
homoveratrylamine (0.7 g, 3.86 mmol) and 2-benzamidobutanoic acid (0.801 g, 3.87 mmol). Yield 75.5% (1.08 g),
–1
mp 132–134°Ñ (Me CO), R 0.79. IR spectrum (ν, cm ): 3468, 3414, 3296 (NH), 3072, 2927, 2871 (Ar-CH), 1652, 1628
2
f
1
(N-C=O), 1544, 1529. Í NMR spectrum (400 MHz, ÑDCl , δ, ppm, J/Hz): 0.86 (3Í, t, J = 7.4, Í-4′), 1.67 (1Í, m, Í-3′a),
3
1.87 (1Í, m, Í-3′b), 2.70 (2Í, t, J = 7.2, Í-α), 3.39 (1Í, m, Í-β), 3.50 (1Í, m, Í-β), 3.74 (3Í, s, OCH ), 3.75 (3Í, s, OCH ),
3
3
4.55 (1Í, q, J = 7.7, H-2′), 6.62 (1Í, d, J = 1.9, Í-2), 6.64 (1Í, d, J = 7.4, Í-5), 6.66 (1Í, dd, J = 1.8, 7.4, Í-6), 6.89 (1H, t,
J = 6.3, NH-β), 7.10 (1Í, d, J = 8, NH-8′′), 7.35 (2Í, t, J = 7.2, H-3′′, 5′′), 7.43 (1Í, tt, J = 1.3, 7.5, H-4′′), 7.73 (2Í, dd,
J = 1.4, 7.2, H-2′′, 6′′).
α-Benzoylamino-N-[2-(3,4-dimethoxyphenyl)ethyl]valeramide (3d), C
H N O , was prepared from
22 28 2 4
homoveratrylamine (0.6 g, 3.3 mmol) and 2-benzamidopentanoic acid (0.734 g, 3.3 mmol). Yield 77.4% (0.986 g),
–1
mp 107–110°Ñ (Me CO), R 0.74. IR spectrum (ν, cm ): 3305 (NH), 3076, 2924, 2870 (Ar-CH), 1653, 1629 (N-C=O), 1549,
2
f
1
1529. Í NMR spectrum (400 MHz, ÑDCl , δ, ppm, J/Hz): 0.84 (3Í, t, J = 7.4, Í-5′), 1.28 (2Í, q, J = 8, Í-4′), 1.61 (1Í, m,
3
Í-3′), 1.80 (1Í, m, Í-3′), 2.70 (2Í, t, J = 7, Í-α), 3.41 (1Í, m, Í-β), 3.50 (1Í, m, Í-β), 3.76 (3Í, s, ÎÑÍ ), 3.78 (3Í, s,
3
ÎÑÍ ), 4.52 (1Í, q, J = 7.5, Í-2′), 6.41 (1Í, br.s, NH-β), 6.62 (1Í, d, J = 1.8, Í-2), 6.65 (1Í, d, J = 8.0, Í-5), 6.67 (1Í, dd,
3
J = 8.7, 1.8, Í-6), 6.81 (1Í, d, J = 8, NH-8′′), 7.37 (2Í, t, J = 7.6, Í-3′′, 5′′), 7.45 (1Í, tt, J = 2.1, 7.4, Í-4′′), 7.71 (2Í, dt, J = 7.1,
1.5, Í-2′′, 6′′).
α-Benzoylamino-β-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]butyramide (3e), C H N O , was prepared from
22 28
2 4
homoveratrylamine (0.65 g, 3.6 mmol) and 2-benzamido-3-methylbutanoic acid (0.8 g, 3.6 mmol). Yield 80% (1.1 g),
–1
mp 164–166°Ñ (Me CO), R 0.77. IR spectrum (ν, cm ): 3304 (NH), 3073, 2959, 2862 (Ar-CH), 1652, 1631 (N-C=O), 1545,
2
f
1
1523. Í NMR spectrum (400 MHz, ÑDCl , δ, ppm, J/Hz): 0.90 (6Í, dd, J = 1.8, 6.7, Í-4′, 5′), 2.10 (1Í, m, Í-3′), 2.70 (2Í,
3
t, J = 7.1, H-α), 3.40 (1Í, m, Í-β), 3.53 (1Í, m, Í-β), 3.76 (3Í, s, OCH ), 3.78 (3Í, s, OCH ), 4.34 (1Í, dd, J = 1.4, 7.3,
3
3
H-2′), 6.41 (1Í, t, J = 6, NH-β), 6.63 (1Í, d, J = 2.0, Í-2), 6.67 (1Í, dd, J = 2.0, 8.3, Í-6), 6.68 (1Í, d, J = 8.6, Í-5), 6.89 (1H,
d, J = 8.7, NH-8′′), 7.37 (2Í, tt, J = 1.2, 7.6, H-3′′, 5′′), 7.45 (1Í, dt, J = 7.4, 1.4, H-4′′), 7.73 (2Í, dt, J = 1.4, 7.0, H-2′′, 6′′).
α-Benzoylamino-N-[2-(3,4-dimethoxyphenyl)ethyl]caproamide (3f), C
H N O , was prepared from
23 30 2 4
homoveratrylamine (0.8 g, 4.4 mmol) and 2-benzamidohexanoic acid (1 g, 4.4 mmol). Yield 73% (1.28 g), mp 131–133°Ñ
–1
(Me CO), R 0.76. IR spectrum (ν, cm ): 3361, 3272 (NH), 3107, 2931, 2859 (Ar-CH), 1657, 1634 (N-C=O), 1577, 1537.
2
f
1
Í NMR spectrum (400 MHz, ÑDCl , δ, ppm, J/Hz): 0.81 (3Í, t, J = 7.1, Í-6′), 1.24 (4Í, m, Í-4′, 5′), 1.62 (2Í, m, Í-3′),
3
2.71 (2Í, t, J = 7, Í-α), 3.42 and 3.49 (1Í each, m, Í-β), 3.76 (3Í, s, OCH ), 3.78 (3Í, s, OCH ), 4.48 (1Í, q, J = 6.8, H-2′),
3
3
6.33 (1Í, t, J = 7.2, NH-β), 6.63–6.68 (3H, m, H-2, 5, 6), 6.76 (1H, d, J = 7.4, NH-8′′), 7.37 (2Í, tt, J = 1.3, 7.3, H-3′′, 5′′), 7.46 (1Í, tt,
702