The Journal of Organic Chemistry
Article
N-Benzylacetamide (11)21: white powder (0.362 g, 81%); mp =
62−64 °C; UV (λmax) = 213 nm; IR ν (cm−1) 3294, 1647, 1545, 1499,
1374, 1357, 1282, 1067, 1032, 751, 741, 696, 606, 503; 1H NMR (400
MHz; CDCl3) δ 7.33−7.24 (m, 5H), 6.21 (br, 1H), 4.37 (d, 2H, J =
5.5 Hz), 1.97 (s, 3H); 13C NMR (100 MHz; CDCl3) δ 170.0, 138.1,
128.5, 127.7, 127.3, 43.5, 23.0; HRMS (ESI) m/z calcd for C9H12NO
[M + H]+ = 150.0919, observed [M + H]+ = 150.0910.
0.95 (t, 3H, J = 7.32 Hz); 13C NMR (100 MHz; DMSO-d6) δ 167.5,
134.7, 131.2, 128.4, 126.7, 39.7, 31.6, 20.1, 13.7; HRMS (ESI) m/z
calcd for C11H16NO [M + H]+ = 178.1232, observed [M + H]+ =
178.1236.
N-Benzyloctanamide (20)59: white powder (0.643 g, 92%); mp =
70−72 °C; UV (λmax) = 213 nm; IR ν (cm−1) 3291, 2921, 2854, 1632,
1
1553, 1444, 732, 692; H NMR (400 MHz; CDCl3) δ 7.35−7.26 (m,
N-Cyclohexylacetamide (12)54: white powder (0.321 g, 76%); mp
= 109−111 °C; IR ν (cm−1) 3290, 2932, 2851, 1639, 1557, 1443,
1373, 1314, 1154, 1116, 980, 892, 736, 606, 550; 1H NMR (400 MHz;
CDCl3) δ 5.68 (br, 1H), 3.76−3.66 (m, 1H), 1.92 (s, 3H), 1.88 (dd,
2H, J = 9.16 Hz), 1.70−1.55 (m, 3H), 1.37−1.28 (m, 2H), 1.17−1.04
(m, 3H); 13C NMR (100 MHz; CDCl3) δ 169.1, 48.1, 33.0, 25.4, 24.8,
23.0; HRMS (ESI) m/z calcd for C8H16NO [M + H]+ = 142.1232,
observed [M + H]+ = 142.1232.
5H), 5.83 (br, 1H), 4.44 (d, 2H, J = 5.96 Hz), 2.21 (t, 2H, J = 7.8 Hz),
1.69−1.61 (q, 2H), 1.30−1.27 (m, 8H), 0.88 (t, 3H, J = 6.84 Hz); 13C
NMR (100 MHz; CDCl3) δ 173.0, 138.3, 128.6, 127.7, 127.4, 43.5,
36.7, 31.6, 29.2, 28.9, 25.7, 22.5, 14.0; HRMS (ESI) m/z calcd for
C15H24NO [M + H]+ = 234.1858, observed = 234.1861.
4-Octanamidobenzoic acid (21)60: white powder (0.702 g, 89%);
mp = 176−178 °C; UV (λmax) = 214 nm; IR ν (cm−1) 3319, 2924,
2855, 1666, 1607, 1591, 1519, 1509, 1427, 1404, 1322, 1300, 1250,
1
2-Acetamido-3-phenylpropanoic acid (13)44: white powder
(0.558 g, 90%); mp = 170−174 °C; UV (λmax) = 206 nm; IR ν
(cm−1) 3329, 1697, 1624, 1555, 1438, 1276, 1243, 1117, 707; 1H
NMR (400 MHz; DMSO-d6) δ 12.66 (br, 1H), 8.18 (d, 1H, J = 8.24
Hz), 7.29−7.18 (m, 5H), 4.42−4.36 (m, 1H, CH), 3.03 and 2.82 (dd
and dd, 2H, J = 9.16 Hz and J = 4.12 Hz), 1.77 (s, 3H); 13C NMR
(100 MHz; DMSO-d6) δ 173.1, 169.2, 137.7, 129.0, 128.1, 126.3, 53.4,
1181, 769; H NMR (400 MHz; DMSO-d6) δ 12.62 (br, 1H), 10.17
(s, 1H), 7.86 (d, 2H, J = 8.68 Hz), 7.70 (d, 2H, J = 9.16 Hz), 2.32 (t,
2H, J = 7.5 Hz), 1.58 (t, 2H, J = 7.12 Hz), 1.27−1.23 (m, 8H), 0.84 (t,
3H, J = 6.88 Hz); 13C NMR (100 MHz; DMSO-d6) δ 171.8, 166.9,
143.4, 130.3, 124.8, 118.2, 36.5, 31.2, 28.5, 25.0, 22.1, 13.9; HRMS
(ESI) m/z calcd for C15H22NO3 [M + H]+ = 264.1600, observed =
264.1604.
36.7, 22.3; HRMS (ESI) m/z calcd for C11H14NO3 [M + H]+
=
N-(4-Methoxyphenyl)dodecanamide (22): white powder (0.713 g,
78%); mp = 90−92 °C; UV (λmax) = 249 nm; IR ν (cm−1) 3238, 2928,
208.0974, observed [M + H]+ = 208.0969.
1
N-(2-Hydroxy-2-phenylethyl)acetamide (14)54: colorless oil (0.434
g, 81%); UV (λmax) = 202 nm; IR ν (cm−1) 3280, 2929, 1646, 1547,
1373, 1295, 1215, 1073, 1041, 754, 668; 1H NMR (400 MHz; DMSO-
d6) δ 8.23 (d, 1H, J = 8.24 Hz), 7.30−7.19 (m, 5H), 4.86−4.79 (m,
2H), 3.52 (t, 2H, J = 6.18 Hz), 1.86 (s, 3H); 13C NMR (100 MHz;
DMSO-d6) δ 168.8, 141.4, 128.0, 126.9, 126.7, 64.7, 54.9, 22.7; HRMS
(ESI) m/z calcd for C10H14NO2 [M + H]+ = 180.1025, observed [M +
H]+ = 180.1024.
2851, 1626, 1638, 1577, 1560, 1453, 1330, 1082, 700; H NMR (400
MHz; CDCl3) δ 7.41 (d, 2H, J = 9.16 Hz), 6.84 (d, 2H, J = 16 Hz),
3.78 (s, 3H), 2.35−2.30 (m, 2H), 1.74−1.67 (m, 2H), 1.25 (br, 16H),
0.88 (t, 3H, J = 6.88 Hz); 13C NMR (100 MHz; CDCl3) δ 171.4,
156.2, 131.0, 121.7, 114.0, 55.4, 37.6, 33.9, 31.8, 29.5, 29.3, 25.7, 22.6,
14.0; HRMS (ESI) m/z calcd for C19H32NO2 [M + H]+ = 306.2433,
observed = 306.2431.
(S)-Methyl 2-dodecanamido-3-(1H-indol-3-yl)propanoate (23)61:
colorless oil (0.996 g, 83%); UV (λmax) = 221 nm; IR ν (cm−1) 3305,
2924, 2852, 1737, 1652, 1517, 1458, 1370, 1236, 1100, 1044, 912, 733;
1H NMR (400 MHz; CDCl3) δ 8.30 (br, 1H), 7.53 (d, 1H, J = 7.8
Hz), 7.36 (d, 1H, J = 8.2 Hz), 7.19 (t, 1H, J = 7.56 Hz), 7.11 (t, 1H, J
= 7.56 Hz), 6.97 (d, 1H, J = 1.8 Hz), 6.01 (d, 1H, J = 7.8 Hz), 6.99−
6.95 (m, 1H), 3.69 (s, 3H), 3.33−3.31 (m, 2H), 2.14 (t, 2H, J = 7.8
Hz), 1.56 (t, 2H, J = 7.34 Hz), 1.24 (br, 16H), 0.88 (t, 3H, J = 6.64
Hz); 13C NMR (100 MHz; CDCl3) δ 172.8, 172.5, 122.6, 122.1,
119.8, 118.5, 111.2, 110.0, 52.8, 52.3, 36.5, 31.8, 29.6, 29.5, 29.4, 29.2,
29.1, 27.6, 25.4, 22.6, 14.1; HRMS (ESI) m/z calcd for C24H37N2O3
[M + H]+ = 401.2804, observed = 401.2795.
N,N′,N″-(Nitrilotris(ethane-2,1-diyl))triacetamide (15): yellowish
oil (0.473 g, 84%); IR ν (cm−1) 3282, 1633, 1546, 1435, 1371, 1291,
1
1169, 749; H NMR (400 MHz; DMSO-d6) δ 7.78 (t, 3H, J = 5.72
Hz), 3.07−3.02 (q, 6H, J = 5.96 Hz), 2.44 (t, 6H, J = 6.4 Hz), 1.80 (s,
9H); 13C NMR (100 MHz; DMSO-d6) δ 169.7, 53.5, 37.1, 22.7;
HRMS (ESI) m/z calcd for C12H25N4O3 [M + H]+ = 273.1927,
observed [M + H]+ = 273.1930.
N-(4-Methoxyphenyl)benzamide (16)55: white powder (0.681 g,
82%); mp > 320 °C; UV (λmax) = 223 and 277 nm; IR ν (cm−1) 3330,
1
1646, 1529, 1514, 1414, 1270, 1249, 1032, 825, 716; H NMR (400
MHz; CDCl3) δ 7.86 (d, 3H, J = 7.36 Hz), 7.55−7.45 (m, 5H), 6.90
(d, 2H, J = 8.68 Hz), 3.81 (s, 3H); 13C NMR (100 MHz; CDCl3) δ
160.3, 156.5, 134.9, 131.6, 130.9, 128.7, 126.9, 122.1, 114.1, 55.4;
HRMS (ESI) m/z calcd for C14H14NO2 [M + H]+ = 228.1025,
observed = 228.1048.
ASSOCIATED CONTENT
■
S
* Supporting Information
1H and 13C NMR spectra of all N-acylated amines (1−24).
This material is available free of charge via the Internet at
N-Cyclohexylbenzamide (17)56: white powder (0.535 g, 88%); mp
= 151−153 °C; UV (λmax) = 224 nm; IR ν (cm−1) 3238, 2928, 2851,
1
1638, 1626, 1577, 1560, 1453, 1330,1089, 700; H NMR (400 MHz;
CDCl3) δ 7.76−7.74 (m, 2H), 7.50−7.40 (m, 3H), 6.01 (d, 1H, J =
4.56 Hz), 4.03−3.93 (m, 1H), 2.03 (dd, 2H, J = 8.72 Hz), 1.78−1.63
(m, 4H), 1.48−1.37 (m, 2H), 1.29−1.18 (m, 3H); 13C NMR (100
MHz; CDCl3) δ 166.6, 135.0, 131.2, 128.4, 126.7, 48.6, 33.2, 25.5,
24.8; HRMS (ESI) m/z calcd for C13H18NO [M + H]+ = 204.1388,
observed = 204.1393.
AUTHOR INFORMATION
Corresponding Author
Notes
■
Phenyl(piperidin-1-yl)methanone (18)57: colorless oil (0.408 g,
72%); UV (λmax) = 224 nm; IR ν (cm−1) 2929, 2856, 1736, 1632,
The authors declare no competing financial interest.
1
ACKNOWLEDGMENTS
1442, 1371, 1277, 1237, 1043, 913, 775, 729; H NMR (400 MHz;
■
CDCl3) δ 7.97 (d, 2H, J = 7.32 Hz), 7.45 (t, 1H, J = 6.2 Hz), 7.32 (t,
2H, J = 7.8 Hz), 3.6 (br, 2H), 3.2 (br, 2H), 1.80 (d, 1H, J = 12 Hz),
1.39 (br, 2H), 1.25−0.97 (m, 3H); 13C NMR (100 MHz; CDCl3) δ
170.4, 136.1, 133.2, 129.9, 129.3, 128.3, 126.7, 49.2, 48.7, 26.4, 25.4,
We thank the Department of Science and Technology,
Government of India, for financial support. S.M.M. is thankful
to CSIR, Government of India, for the Senior Research
Fellowship.
24.7, 24.4; HRMS (ESI) m/z calcd for C12H16NO [M + H]+
=
190.1232, observed = 190.1229.
N-Butylbenzamide (19)58: colorless oil (0.472 g, 89%); UV (λmax
)
REFERENCES
■
= 224 nm; IR ν (cm−1) 3317, 2959, 2930, 2867, 1639, 1542, 1489,
1460, 1306, 701; 1H NMR (400 MHz; CDCl3) δ 7.75 (d, 2H, J = 8.72
Hz), 7.50−7.39 (m, 3H), 6.27 (br, 1H), 3.47−3.42 (q, 2H, J = 5.96
Hz), 1.63−1.55 (q, 2H, J = 7.32 Hz), 1.45−1.36 (q, 2H, J = 7.32 Hz),
(1) Larock, R. C. Comprehensive Organic Transformations, 2nd ed.;
VCH: Weinheim, Germany, 1989.
(2) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic
synthesis, 3rd ed.; John Wiley & Sons, Inc.: New York, 1999; p 150.
E
dx.doi.org/10.1021/jo400701v | J. Org. Chem. XXXX, XXX, XXX−XXX