The Journal of Organic Chemistry
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141.3, 144.9, 170.4; Found (EI) [M]+ 212.0947 C13H12ON2, requires
212.0944.
5.8, 2H), 5.76 (br s, 1H), 7.18−7.22 (m, 4H), 7.24−7.28 (m, 1H),
7.29−7.32 (m, 4H); δC (150 MHz, CDCl3) 43.1, 43.8, 127.69, 127.74,
128.9, 129.2, 130.9, 133.3, 133.5, 138.1, 170.4.
N-(Pyridin-2-yl)-2-phenylacetamide (2u).49 Purified by column
chromatography (EtOAc:PE 3:1, 10% NEt3). White solid (25 mg,
12%): mp 121−122 °C (CH2Cl2) [lit.49 122−124 °C]; νmax (solid/
cm−1) 3230 (N−H), 3046, 2959, 2921 (C−H), 1656 (CO); δH
(500 MHz, CDCl3) 3.74 (s, 2H), 6.98−7.03 (m, 1H), 7.27−7.33 (m,
3H), 7.33−7.38 (m, 2H), 7.66−7.71 (m, 1H), 8.19−8.27 (m, 2H),
8.52 (br s, 1H); δC (125 MHz, CDCl3) 45.1, 114.1, 120.0, 127.8,
129.3, 129.6, 134.0, 138.5, 147.7, 151.3, 169.6; Found (ES) [M + H]+
213.1035 C13H13ON2, requires 213.1028.
N-Benzyl-2-(thiophen-3-yl)acetamide (3h). Yellow solid (212 mg,
91%): mp 96−98 °C (CH2Cl2); νmax (solid/cm−1) 3279 (N−H),
3086, 3062, 3032, 2925 (C−H), 1635 (CO); δH (600 MHz,
CDCl3) 3.65 (s, 2H), 4.42 (d, J 5.8, 2H), 5.85 (br s, 1H), 7.01 (d, J 4.8,
1H), 7.14−7.15 (m, 1H), 7.19 (d, J 7.5, 2H), 7.23−7.34 (m, 4H); δC
(150 MHz, CDCl3) 38.3, 43.7, 123.7, 127.0, 127.61, 127.62, 128.6,
128.8, 134.8, 138.2, 170.5; Found (ES) [M + H]+ 232.0789
C13H14ONS, requires 232.0796.
N-tert-Butyl-2-phenylacetamide (2v).51 White solid (116 mg,
60%): mp 104−106 °C (CH2Cl2) [lit.51 103 °C]; νmax (solid/cm−1)
3303 (N−H), 3063, 2962, 2872 (C−H), 1638 (CO); δH (600
MHz, CDCl3) 1.28 (s, 9H), 3.48 (s, 2H), 5.17 (br s, 1H), 7.24 (d, J
7.2, 2H), 7.26−7.30 (m, 1H), 7.35 (t, J 7.4, 2H); δC (150 MHz,
CDCl3) 28.8, 45.0, 51.4, 127.3, 129.1, 129.4, 135.6, 170.4.
N-Benzyl-2-(naphthalen-2-yl)acetamide (3a).52 Yellow solid (225
mg, 81%): mp 168−169 °C (CH2Cl2) [lit.52 170−174 °C]; νmax
(solid/cm−1) 3225 (N−H), 3053, 3030, 2976, 2936 (C−H), 1628
(CO); δH (500 MHz, CDCl3) 3.79 (s, 2H), 4.41 (d, J 5.8, 2H), 5.81
(br s, 1H), 7.18 (d, J 7.0, 2H), 7.21−7.30 (m, 3H), 7.39 (dd, J 8.3, 1.7,
1H), 7.46−7.52 (m, 2H), 7.72 (br s, 1H), 7.78−7.82 (m, 1H), 7.82−
7.85 (m, 2H); δC (125 MHz, CDCl3) 43.7, 44.1, 126.2, 126.5, 127.4,
127.5, 127.6, 127.7, 127.8, 128.4, 128.7, 129.0, 132.3, 132.6, 133.6,
138.2, 170.8.
N-Benzyl-2-(4-phenoxyphenyl)acetamide (3i). Yellow solid (298
mg, 95%): mp 125−126 °C (CH2Cl2); νmax (solid/cm−1) 3285 (N−
H), 3085, 3064, 3033, 2921 (C−H), 1636 (CO); δH (600 MHz,
CDCl3) 3.60 (s, 2H), 4.43 (d, J 5.9, 2H), 5.71 (br s, 1H), 6.96−7.01
(m, 4H), 7.10−7.13 (m, 1H), 7.18−7.21 (m, 2H), 7.21−7.24 (m, 2H),
7.25−7.28 (m, 1H), 7.29−7.36 (m, 4H); δC (150 MHz, CDCl3) 43.2,
43.8, 119.2, 119.3, 123.6, 127.6, 127.7, 128.8, 129.5, 129.9, 130.9,
138.2, 156.8, 157.0, 171.0; Found (EI) [M]+ 317.1416 C21H19O2N,
requires 317.1410.
Boc-Sarcosine-benzamide (3k).58 Yellow solid (265 mg, 95%): mp
82−84 °C (CH2Cl2) [lit.58 83−85 °C]; νmax (solid/cm−1) 3310 (N−
H), 3067, 2978, 2931 (C−H), 1664 (CO), 1685 (CO); δH (400
MHz, CDCl3, 58 °C) 1.40 (s, 9H), 2.90 (s, 3H), 3.83 (s, 2H), 4.41 (d,
J 5.9, 2H), 6.52 (br s, 1H), 7.19−7.24 (m, 3H), 7.25−7.31 (m, 2H); δC
(100 MHz, CDCl3, 58 °C) 28.2, 35.7, 43.3, 53.4, 80.6, 127.3, 127.5,
128.6, 138.2, 155.9, 169.1; Found (EI) [M]+ 278.1629 C15H22O3N2,
requires 278.1625.
(E)-N-Benzyl-3-(thiophen-3-yl)acrylamide (3m). Yellow solid (217
mg, 88%): mp 107−110 °C (CH2Cl2); νmax (solid/cm−1) 3275 (N−
H), 3029, 2971 (C−H), 1739 (CO); δH (600 MHz, CDCl3) 4.55
(d, J 5.7, 2H), 6.05 (br s, 1H), 6.26 (d, J 15.5, 1H), 7.22−7.24 (m,
1H), 7.26−7.36 (m, 6H), 7.42 (d, J 2.1, 1H), 7.65 (d, J 15.5, 1H); δC
(150 MHz, CDCl3) 44.0, 120.2, 125.1, 126.9, 127.4, 127.7, 128.0,
128.9, 135.2, 137.8, 138.3, 166.1; Found (ES+) [M + H]+ 244.0800
C14H14NOS, requires 244.0796.
N-Benzyl-2,2-diphenylacetamide (3b).53 Yellow solid (247 mg,
81%): mp 127−128 °C (CH2Cl2) [lit.53 126−128 °C]; νmax (solid/
cm−1) 3311 (N−H), 3060, 3030, 2930 (C−H), 1634 (CO); δH
(500 MHz, CDCl3) 4.48 (d, J 5.7, 2H), 4.96 (s, 1H), 5.94 (br s, 1H),
7.19−7.22 (m, 2H), 7.24−7.30 (m, 8H), 7.30−7.35 (m, 5H); δC (125
MHz, CDCl3) 43.9, 59.3, 127.4, 127.6, 127.7, 128.8, 128.9, 129.0,
138.2, 139.4, 171.8.
N-Benzyl-2-(4-methoxyphenyl)acetamide (3c).54 Yellow solid
(232 mg, 90%): mp 134−135 °C (CH2Cl2) [lit.54 136 °C]; νmax
(solid/cm−1) 3286 (N−H), 3082, 3063, 3033, 2968, 2838 (C−H),
1635 (CO); δH (600 MHz, CDCl3) 3.57 (s, 2H), 3.79 (s, 3H), 4.40
(d, J 5.8, 2H), 5.75 (br s, 1H), 6.86−6.89 (m, 2H), 7.16−7.19 (m,
4H), 7.23−7.26 (m, 1H), 7.28−7.31 (m, 2H); δC (150 MHz, CDCl3)
43.0, 43.7, 55.4, 114.6, 126.8, 127.5, 127.6, 128.8, 130.7, 138.3, 159.0,
171.5.
(E)-N-Benzyl-2-methyl-3-phenylacrylamide (3n). White solid (229
mg, 90%): mp 120−121 °C (CH2Cl2); νmax (solid/cm−1) 3332 (N−
H), 3079, 3059, 2921, 2852 (C−H), 1531 (CO); δH (600 MHz,
CDCl3) 2.11 (s, 3H), 4.56 (d, J 5.7, 2H), 6.69 (br s, 1H), 7.27−7.40
(m, 11H); δC (150 MHz, CDCl3) 14.5, 44.2, 127.7, 127.98, 128.04,
128.5, 128.9, 129.5, 131.9, 134.3, 136.2, 138.5, 169.6; Found (ES) [M
+ H]+ 252.1394 C17H18ON, requires 252.1388.
N-Benzyl-2-(2-bromophenyl)acetamide (3d).55 Yellow solid (276
mg, 90%): mp 143−144 °C (CH2Cl2) [lit.55 144−145 °C]; νmax
(solid/cm−1) 3272 (N−H), 3055, 3030, 2920, 2871 (C−H), 1642
(CO); δH (600 MHz, CDCl3) 3.77 (s, 2H), 4.44 (d, J 5.7, 2H), 5.75
(br s, 1H), 7.16 (td, J 7.7, 1.7, 1H), 7.21−7.27 (m, 3H), 7.30 (app t, J
7.6, 3H), 7.37 (dd, J 7.5, 1.6, 1H), 7.58 (dd, J 8.0, 1.0, 1H); δC (150
MHz, CDCl3) 43.8, 44.2, 125.0, 127.6, 127.7, 128.2, 128.8, 129.4,
131.9, 133.3, 134.8, 138.1, 169.5.
N-Benzyl-2-(4-bromophenyl)acetamide (3e). Yellow solid (289
mg, 94%): mp 165−166 °C (CH2Cl2); νmax (solid/cm−1) 3280 (N−
H), 3056, 3026, 2917, 2872 (C−H), 1642 (CO); δH (600 MHz,
CDCl3) 3.55 (s, 2H), 4.41 (d, J 5.6, 2H), 5.72 (br s, 1H), 7.15 (d, J 8.4,
2H), 7.19 (d, J 7.0, 2H), 7.25−7.28 (m, 1H), 7.29−7.33 (m, 2H),
7.45−7.48 (m, 2H); δC (150 MHz, CDCl3) 43.2, 43.8, 121.6, 127.7,
127.8, 128.9, 131.2, 132.2, 133.8, 138.0, 170.2; Found (EI) [M]+
303.0256 C15H14ONBr, requires 303.0253.
N-Benzyl-2,2,2-trifluoroacetamide (3p).59 Yellow solid (183 mg,
89%): mp 72−74 °C (CH2Cl2) [lit.59 70−71 °C]; νmax (solid/cm−1)
3300 (N−H), 3110, 3035, 2923 (C−H), 1702 (CO); δH (500
MHz, CDCl3) 4.54 (d, J 5.8, 2H), 6.52 (br s, 1H), 7.28−7.32 (m, 2H),
7.32−7.41 (m, 3H); δC (125 MHz, CDCl3) 43.9, 116.0 (q, J 285.4),
128.0, 128.2, 129.0, 136.1, 157.5 (q, J 36.9); δF (282 MHz, CDCl3)
−76.2.
N-Benzyl-4-methoxybenzamide (3s).60 Yellow solid (172 mg,
71%): mp 129−130 °C (CH2Cl2) [lit.60 129−130 °C]; νmax (solid/
cm−1) 3256 (N−H), 3058, 2957, 2930, 2834 (C−H), 1631 (CO);
δH (500 MHz, CDCl3) 3.85 (s, 3H), 4.64 (d, J 5.7, 2H), 6.28 (br s,
1H), 6.90−6.94 (m, 2H), 7.28−7.32 (m, 1H), 7.36 (m, 4H), 7.74−
7.77 (m, 2H); δC (125 MHz, CDCl3) 44.1, 55.5, 113.8, 126.7, 127.6,
128.0, 128.8, 128.9, 138.5, 162.3, 167.0.
N-Benzyl-2-(3,4-dimethoxyphenyl)acetamide (3f). Brown solid
(235 mg, 81%): mp 100−101 °C (CH2Cl2) [lit.56 98−100 °C]; νmax
(solid/cm−1) 3297 (N−H), 3065, 3033, 3000, 2936, 2835 (C−H),
1634 (CO); δH (600 MHz, CDCl3) 3.58 (s, 2H), 3.85 (s, 3H), 3.86
(s, 3H), 4.41 (d, J 5.6, 2H), 5.74 (br s, 1H), 6.76−6.80 (m, 2H), 6.83
(d, J 8.0, 1H), 7.18 (d, J 7.0, 2H), 7.23−7.26 (m, 1H), 7.28−7.31 (m,
2H); δC (150 MHz, CDCl3) 43.6, 43.7, 55.98, 56.02, 111.6, 112.4,
121.8, 127.2, 127.58, 127.61, 128.8, 138.3, 148.4, 149.4, 171.3; Found
(EI) [M]+ 285.1353 C17H19O3N, requires 285.1359.
N-Benzyl-4-(trifluoromethyl)benzamide (3t).61 Yellow solid (212
mg, 76%): mp 168−170 °C (CH2Cl2) [lit.61 149−151 °C]; νmax
(solid/cm−1) 3326 (N−H), 3091, 3071, 3036 (C−H), 1643 (CO);
δH (600 MHz, CDCl3) 4.65 (d, J 5.6, 2H), 6.53 (br s, 1H), 7.29−7.33
(m, 1H), 7.33−7.38 (m, 4H), 7.68 (d, J 8.2, 2H), 7.89 (d, J 8.2, 2H);
δC (150 MHz, CDCl3) 44.5, 123.7 (q, J 272.5), 125.8 (q, J 3.8), 127.6,
128.0, 128.1, 129.0, 133.4 (q, J 32.7), 137.7, 137.8, 166.2; δF (282
MHz, CDCl3) −63.4.
N,2-Dibenzylbenzamide (3u). Yellow solid (184 mg, 61%): mp
119−120 °C (CH2Cl2); νmax (solid/cm−1) 3296 (N−H), 3057, 3025,
3008, 2921, 2873 (C−H), 1633 (CO), δH (600 MHz, CDCl3) 4.22
(s, 2H), 4.49 (d, J 5.6, 2H), 5.86 (br s, 1H), 7.13 (d, J 7.1, 2H), 7.16−
7.19 (m, 3H), 7.21−7.25 (m, 4H), 7.26−7.32 (m, 3H), 7.33−7.37 (m,
N-Benzyl-2-(4-chlorophenyl)acetamide (3g).57 Yellow solid (244
mg, 93%): mp 157−158 °C (CH2Cl2) [lit.57 151−153 °C]; νmax
(solid/cm−1) 3277 (N−H), 3056, 3027, 2918, 2874 (C−H), 1642
(CO), 690 (C−Cl); δH (600 MHz, CDCl3) 3.56 (s, 2H), 4.41 (d, J
H
dx.doi.org/10.1021/jo400509n | J. Org. Chem. XXXX, XXX, XXX−XXX