38
L.-P. Guan et al.
Arch. Pharm. Chem. Life Sci. 2009, 342, 34–40
a AV-300 (Bruker, Switzerland), and all chemical shifts were
given in ppm relative to tetramethysilane. Microanalyses of C, N,
and H were performed using a Heraeus CHN Rapid Analyzer
(Heraeus, Germany). Mass spectra were measured on an
HP1100LC (Agilent Technologies, USA). The major chemicals
were purchased from Alderich Chemical Corporation. All other
chemicals were the analytical grade.
N-(2-Hydroxyethyl)nonanamide 1f
Yield: 56%; m.p.: 45-478C; IR (KBr) [cm– 1]: 1706 (C=O), 3218 (NH),
1
3320 (OH); H-NMR (CDCl3) [ppm]: 0.87 (t, J = 6.8 Hz, 3H, CH3),
1.28–1.62 (m, 12H, (CH2)6), 2.15 (s, 1H, OH), 2.31 (t, J = 7.5 Hz, 2H,
CH2CO), 3.53 (dd, J = 5.3 Hz, 2H, CH2), 4.16 (t, J = 5.1 Hz, 2H, CH2),
5.77 (s, 1H, NH); MS m/z: 202 [M + 1]. Anal.Calcd. for C11H23NO2: C,
65.63; H, 11.52; N, 6.96. Found: C, 65.51; H, 11.46; N, 6.79.
General procedure for the preparation of 1a–s
N-(2-Hydroxyethyl)decanamide 1g
In a three-necked round-bottomed flask containing substituted
carboxylic acid 2 g (0.05 mol), 50 mL dichlormethane and trie-
thylamine (0.1 mol), methyl chloroformate (0.1 mol) was slowly
added dropwise with stirring and in an ice bath. The mixture
was stirred 2 h at room temperature. Then, ethanolamine
(0.1 mol) was dropwise added with stirring (in an ice bath), the
mixture was stirred 8–10 h at room temperature. The solvents
were removed under reduced pressure. The residue was poured
into 100 mL ice water and stirred for 10 min. The solid obtained
after filtration was recrystallized in hot water to afford a white
solid.
Yield: 81%; m.p.: 78–808C; IR (KBr) [cm– 1]: 1689 (C=O), 3189 (NH),
3321 (OH); 1H-NMR (CDCl3) [ppm]: 0.88 (t, J = 6.7 Hz, 3H,CH3), 1.28-
1.63 (m, 14H, (CH2)7), 1.81 (s, 1H, OH), 2.20 (t, J = 7.5 Hz, 2H,
CH2CO), 3.41 (dd, J = 5.1 Hz, 2H, CH2), 3.70 (t, J = 5.2 Hz, 2H, CH2),
6.07 (s, 1H, NH); MS m/z: 216 [M + 1]. Anal. Calcd. for C12H25NO2:
C, 66.93; H, 11.70; N, 6.50. Found: C, 66.84; H, 11.63; N, 6.41.
N-(2-Hydroxyethyl)undec-10-enamide 1h
Yield: 79%; m.p.: 56–588C; IR (KBr) [cm– 1]: 1695 (C=O), 3211 (NH),
3319 (OH);1H-NMR (CDCl3) [ppm]: 1.27–1.60 (m, 14H, (CH2)7), 1.98
(s, 1H, OH), 2.20 (t, J = 7.4 Hz, 2H, CH2CO), 3.38 (dd, J = 5.1 Hz, 2H,
CH2), 3.67 (t, J = 5.1 Hz, 2H, CH2), 4.92 (t, J = 10.6 Hz, 2H, =CH2),
5.77 (m, 1H, =CH), 6.46 (s, 1H, NH); MS m/z: 228 [M + 1]. Anal.
Calcd. for C13H25NO2: C, 68.68; H, 11.08; N, 6.16. Found: C, 68.56;
H, 10.87; N, 5.91.
N-(2-Hydroxyethyl) propionamide 1a
Yield: 56%; m.p.: 46–488C; IR (KBr) [cm– 1]: 1678 (C=O), 3120 (NH),
3309 (OH); 1H-NMR (CDCl3) [ppm]: 1.15 (t, J = 6.1 Hz, 3H, CH3), 1.97
(s, 1H, OH), 2.23 (t, J = 7.1 Hz, 2H, CH2CO), 3.37 (dd, J = 5.1 Hz, 2H,
CH2), 3.79 (t, J = 4.8 Hz, 2H, CH2), 6.08 (s, 1H, NH); MS m/z: 118 [M
+ 1]. Anal. Calcd. for C5H11NO2: C, 51.26; H, 9.46; N, 11.96. Found:
C, 51.19; H, 9.34; N, 11.82.
N-(2-Hydroxyethyl)dodecanamide 1i
Yield: 77%; m.p.: 76–788C; IR (KBr) [cm– 1]: 1692 (C=O), 3123 (NH),
1
N-(2-Hydroxyethyl)butyramide 1b
3314 (OH); H-NMR (CDCl3) [ppm]: 0.88 (t, J = 6.9 Hz, 3H, CH3),
Yield: 54%; m.p.: 49–518C; IR (KBr) [cm– 1]: 1682 (C=O), 3124 (NH),
3305 (OH);1H-NMR (CDCl3) [ppm]: 0.95 (t, J = 6.7 Hz, 3H, CH3), 1.61
(m, 2H, CH2), 2.03 (s, 1H, OH), 2.19 (t, J = 7.3 Hz, 2H, CH2CO), 3.41
(dd, J = 4.5 Hz, 2H, CH2), 3.78 (t, J = 4.9 Hz, 2H, CH2), 6.09 (s, 1H,
NH); MS m/z: 132 [M + 1]. Anal. Calcd. for C6H13NO2: C, 54.94; H,
9.99; N, 10.68. Found: C, 54.86; H, 9.88; N, 10.54.
1.26-1.64 (m, 18H, (CH2)9), 1.92 (s, 1H, OH), 2.21 (t, J = 7.5 Hz, 2H,
CH2CO), 3.42 (dd, J = 5.3 Hz, 2H, CH2), 3.73 (t, J = 4.8 Hz, 2H, CH2),
6.04 (1H, s, NH); MS m/z: 244 [M + 1]. Anal. Calcd. for C14H29NO2:
C, 69.09; H, 12.01; N, 5.75. Found: C, 68.89; H, 11.90; N, 5.63.
N-(2-Hydroxyethyl)tetradecanamide 1j
Yield: 75%; m.p.: 88–918C; IR (KBr) [cm– 1]: 1695 (C=O), 3087 (NH),
3321 (OH); H-NMR (CDCl3) [ppm]: 0.89 (t, J = 6.9 Hz, 3H, CH3),
1.26–1.64 (m, 22H, (CH2)11), 1.98 (s, 1H, OH), 2.24 (t, J = 7.6 Hz, 2H,
CH2CO), 3.42 (dd, J = 5.3 Hz, 2H, CH2), 3.73 (t, J = 4.8 Hz, 2H, CH2),
6.05 (s, 1H, NH); MS m/z: 272 [M + 1]. Anal. Calcd. for C16H33NO2:
C, 70.80; H, 12.25; N, 5.16. Found: C, 70.71; H, 12.10; N, 5.02.
N-(2-Hydroxyethyl)pentanamide 1c
1
Yield: 49%; m.p.: 53–558C; IR (KBr) [cm– 1]: 1700 (C=O), 3017 (NH),
1
3310 (OH); H-NMR (CDCl3) [ppm]: 0.92 (t, J = 7.3 Hz, 3H, CH3),
1.25–1.63 (m, 4H, (CH2)2), 2.16 (s, 1H, OH), 2.22 (t, J = 7.2 Hz, 2H,
CH2CO), 3.44 (dd, J = 5.1 Hz, 2H, CH2), 3.74 (t, J = 4.8 Hz, 2H, CH2),
5.89 (s, 1H, NH); MS m/z: 146 [M + 1]. Anal. Calcd. for C7H15NO2: C,
57.90; H, 10.41; N, 9.65. Found: C, 57.81; H, 10.28; N, 9.53.
N-(2-Hydroxyethyl)pentadecanamide 1k
N-(2-Hydroxyethyl)hexanamide 1d
Yield: 79%; m.p.: 85–888C; IR (KBr) [cm– 1]: 1703 (C=O), 3198 (NH),
Yield: 50%; m.p.: 47–498C; IR (KBr) [cm– 1]: 1702 (C=O), 3204 (NH),
1
3318 (OH); H-NMR (CDCl3) [ppm]: 0.89 (t, J = 6.1 Hz, 3H, CH3),
1
3311(OH); H-NMR (CDCl3) [ppm]: 0.89 (t, J = 6.2 Hz, 3H, CH3),
1.26–1.64 (m, 24H, (CH2)12), 1.97 (s, 1H, OH), 2.22 (t, J = 7.4 Hz, 2H,
CH2CO), 3.43 (dd, J = 5.2 Hz, 2H, CH2), 3.74 (t, J = 5.0 Hz, 2H, CH2),
5.97 (s, 1H, NH); MS m/z: 286 [M + 1]. Anal. Calcd. for C17H35NO2:
C, 71.53; H, 12.36; N, 4.91. Found: C, 71.41; H, 12.20; N, 4.81.
1.29–1.63 (m, 6H, (CH2)3), 2.15 (s, 1H, OH), 2.17 (t, J = 7.8 Hz, 2H,
CH2CO), 3.40 (dd, J = 5.2 Hz, 2H, CH2), 3.73 (t, J = 4.9 Hz, 2H, CH2),
6.12 (s, 1H, NH); MS m/z: 160 [M + 1]. Anal. Calcd. for C8H17NO2: C,
60.35; H, 10.76; N, 8.80. Found: C, 60.23; H, 10.61; N, 8.71.
N-(2-Hydroxyethyl)octanamide 1e
N-(2-Hydroxyethyl)palmitamide 1l
Yield: 53%; m.p.: 44–468C; IR (KBr) [cm– 1]: 1696 (C=O), 3110 (NH),
Yield: 82%; m.p.: 95–968C; IR (KBr) [cm– 1]: 1701 (C=O), 3210 (NH),
1
1
3319 (OH); H-NMR (CDCl3) [ppm]: 0.89 (t, J = 6.8 Hz, 3H, CH3),
3320 (OH); H-NMR (CDCl3) [ppm]: 0.88 (t, J = 6.1 Hz, 3H, CH3),
1.28–1.63 (m, 10H, (CH2)5), 2.16 (s, 1H, OH), 2.32 (t, J = 7.6 Hz, 2H,
CH2CO), 3.51 (dd, J = 5.4 Hz, 2H, CH2), 4.13 (t, J = 5.3 Hz, 2H, CH2),
5.89 (s, 1H, NH); MS m/z: 188 [M + 1]. Anal. Calcd. for C10H21NO2:
C, 64.13; H, 11.30; N, 7.48. Found: C, 64.01; H, 11.12; N, 7.29.
1.25–1.63 (m, 26H, (CH2)13), 1.98 (s, 1H, OH), 2.21 (t, J = 7.5 Hz, 2H,
CH2CO), 3.44 (dd, J = 5.1 Hz, 2H, CH2), 3.73 (t, J = 4.9 Hz, 2H, CH2),
5.94 (s, 1H, NH); MS m/z: 300 [M + 1]. Anal. Calcd. for C18H37NO2:
C, 72.19; H, 12.45; N, 4.68. Found: C, 72.01; H, 12.34; N, 4.50.
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