194 J. HOOPER AND P. WATTS
tubing and syringes were all purchased from Supelco.
The syringe driver (MD-1001) was manufactured by
Bioanalytical Systems Inc. and could operate at set flow
m, Ar) and 7.32 (2 H, m, 2 ꢀ Ar); dC (100 MHz, CDCl3/
TMS) 23.3 (CH3), 35.6 (CH2), 40.6 (CH2), 126.5 (CH),
128.6 (2 ꢀ CH), 128.7 (2 ꢀ CH), 138.8 (C0) and 170.0
(CO); m/z (EI) 164 (Mþ þ 1, 100%), 104 (37) and 65 (6).
N-Phenyl-benzamide (15).16 (0.37 g, 37%) as fine
white crystals; dH (400 MHz, CDCl3/TMS) 7.16 (1 H,
m, Ar), 7.38 (2 H, m, 2 ꢀ Ar), 7.50 (2 H, m, 2 ꢀ Ar), 7.56
(1 H, m, Ar), 7.65 (2 H, m, 2 ꢀ Ar), 7.79 (1 H, br s, NH)
and 7.88 (2 H, m, 2 ꢀ Ar); dC (100 MHz, CDCl3/TMS)
120.2 (2 ꢀ CH), 124.6 (CH), 127.0 (2 ꢀ CH), 128.9
(2 ꢀ CH), 129.1 (2 ꢀ CH), 131.9 (CH), 135.0 (C0), 137.9
(C0) and 165.7 (CO); m/z (EI) 198 (Mþ þ 1, 46%), 197
(100), 105 (68) and 51 (4).
rates ranging between 0.1 and 100 ml minꢁ1
.
General batch preparation methodology
To a stirred solution of pre-weighed amine dissolved in
DCM (150 ml) was added an equimolar amount of
acylating agent (acetyl chloride 2 or benzoyl chloride
13). After 2 h continued stirring at room temperature
any solids were removed by filtration and the reaction
mixture was washed with sat. NH4Cl solution
(3 ꢀ 150 ml). The organic layer was dried over anhy-
drous MgSO4, filtered and concentrated in vacuo.
Subsequent recrystallization (DCM or ether/hexane)
yielded the corresponding amide, confirmed by com-
parison to data in the literature.
N-Phenyl-acetamide (4).12 (0.27 g, 27%) as fine white
needles; dH (400 MHz, CDCl3/TMS) 2.18 (3 H, s, CH3),
7.10 (1 H, m, Ar), 7.31 (2 H, m, 2 ꢀ Ar), 7.36 (1 H, br s,
NH) and 7.50 (2 H, m, 2 ꢀ Ar); dC (100 MHz, CDCl3/
TMS) 24.6 (CH3), 119.9 (CH), 124.3 (2 ꢀ CH), 129.0
(2 ꢀ CH), 137.9 (C0) and 168.3 (CO); m/z (EI) 136
(Mþ þ 1, 30%), 135 (84), 93 (100) and 65 (6).
N-(4-Methoxy-phenyl)-benzamide (16).17 (0.2235 g,
22%) as white crystals; dH (400 MHz, CDCl3/TMS)
3.81 (3 H, s, CH3), 6.91 (2 H, d, J 9.0, 2 ꢀ Ar), 7.47
(2 H, m, 2 ꢀ Ar), 7.54 (3 H, m, 3 ꢀ Ar), 7.76 (1 H, br s,
NH) and 7.86 (2 H, d, J 7.0, 2 ꢀ Ar); dC (100 MHz,
CDCl3/TMS) 55.5 (2 ꢀ CH), 114.2 (2 ꢀ CH), 122.1
(2 ꢀ CH), 127.0 (2 ꢀ CH), 128.7 (2 ꢀ CH), 131.0 (C0),
131.7 (C0), 135.0 (CH), 156.6 (C0) and 165.6 (CO); m/z
(EI) 228 (Mþ þ 1, 15%), 227 (93), 105 (100), 77 (57) and
51 (19).
N-(3-Acetyl-phenyl)-benzamide
(14).18 (0.2770 g,
28%) as faint pink crystals; dH (400 MHz, CDCl3/TMS)
2.61 (3 H, s, CH3), 7.49 (3 H, m, 3 ꢀ Ar), 7.57 (1 H, m,
Ar), 7.73 (1 H, ddd, J 7.9, J 1.7 and J 1.1, Ar), 7.91 (2 H,
m, 2 ꢀ Ar), 8.07 (1 H, ddd, J 8.2, J 2.2 and J 1.1, Ar),
8.17 (1 H, t, J 2.0, Ar) and 8.19 (1 H, br s, NH); dC
(100 MHz, CDCl3/TMS) 26.7 (CH3), 119.6 (CH), 124.4
(CH), 124.8 (CH), 127.1 (2 ꢀ CH), 128.8 (2 ꢀ CH), 129.4
(CH), 132.1 (CH), 134.6 (C0), 137.8 (C0), 138.5 (C0),
165.9 (CO) and 197.9 (CO); m/z (EI) 240 (Mþ þ 1, 10%),
239 (65), 105 (100), 77 (57) and 51 (15).
N-Benzyl-benzamide (17).19 (0.1069 g, 10.7%) as fine
white crystals; dH (400 MHz, CDCl3/TMS) 4.64 (2 H, d,
J 6.0, CH2), 6.46 (1 H, br s, NH), 7.31 (1 H, m, 1 ꢀ Ar),
7.35 (4 H, d, J 4.5, 4 ꢀ Ar), 7.42 (2 H, m, 2 ꢀ Ar), 7.50
(1 H, m, Ar) and 7.79 (2 H, m, 2 ꢀ Ar); dC (100 MHz,
CDCl3/TMS) 44.1 (CH2), 126.9 (2 ꢀ CH), 127.6 (CH),
127.9 (2 ꢀ CH), 128.6 (2 ꢀ CH), 128.8 (2 ꢀ CH), 131.5
(CH), 134.4 (C0), 138.2 (C0) and 167.3 (CO); m/z (EI)
212 (Mþ þ 1, 26%), 211 (100), 105 (96), 77 (80) and
51 (28).
N-Phenethyl-benzamide (18).20 (0.27 g, 27%) as fine
white crystals; dH (400 MHz, CDCl3/TMS) 2.94 (2 H, t, J
7.0, CH2), 3.73 (2 H, m, CH2), 6.15 (H, br s, NH), 7.25
(3 H, m, 3 ꢀ Ar), 7.33 (2 H, m, 2 ꢀ Ar), 7.40 (2 H, m,
2 ꢀ Ar), 7.48 (H, m, Ar) and 7.68 (2 H, m, 2 ꢀ Ar); dC
(100 MHz, CDCl3/TMS) 35.7 (CH2), 41.1 (CH2), 126.6
(CH), 126.8 (2 ꢀ CH), 128.5 (2 ꢀ CH), 128.7 (2 ꢀ CH),
128.8 (2 ꢀ CH), 131.4 (CH), 134.7 (C0), 138.9 (C0) and
167.4 (CO); m/z (EI) 226 (Mþ þ 1, 10%), 134 (20), 105
(100), 77 (46) and 51 (18).
N-(4-Methoxy-phenyl)-acetamide (9).12 (0.21 g, 21%)
as white crystals; dH (400 MHz, CDCl3/TMS) 2.15 (3 H,
s, CH3), 3.78 (3 H, s, CH3), 6.85 (2 H, d, J 9.0, 2 ꢀ Ar),
7.19 (1 H, br s, NH) and 7.38 (2 H, d, J 9.0, 2 ꢀ Ar); dC
(100 MHz, CDCl3/TMS) 24.3 (CH3), 55.5 (CH3), 114.1
(2 ꢀ CH), 121.9 (2 ꢀ CH), 130.9 (C0), 156.4 (C0)
and 168.1 (CO); m/z (EI) 166 (Mþ þ 1, 100%) and
108 (20).
N-(3-Acetyl-phenyl)-acetamide (10).13 (0.12 g, 12%) as
white crystals; dH (400 MHz, CDCl3/TMS) 2.22 (3 H, s,
CH3), 2.61 (3 H, s, CH3), 7.43 (2 H, t and br s, J 7.8, Ar
and NH), 7.70 (1 H, m, Ar), 7.90 (1 H, m, Ar) and 8.00
(1 H, m, Ar); dC (100 MHz, CDCl3/TMS) 24.6 (CH3), 26.7
(CH3), 119.2 (CH), 124.2 (CH), 124.5 (CH), 129.4 (CH),
137.7 (C0), 138.4 (C0), 168.5 (CO) and 197.9 (CO); m/z
(EI) 178 (Mþ þ 1, 48%), 177 (100), 135 (55), 120 (70),
87 (15) and 63 (15).
N-Benzyl-acetamide (11).14 (0.13 g, 13%) as a white
crystalline solid; dH (400 MHz, CDCl3/TMS) 2.02 (3 H,
s, CH3), 4.43 (2 H, d, J 5.6, CH2), 5.85 (1 H, br s, NH)
and 7.28 (3 H, m, 3 ꢀ Ar) and 7.34 (2 H, m, 2 ꢀ Ar); dC
(100 MHz, CDCl3/TMS) 23.3 (CH3), 43.8 (CH2), 127.5
(CH), 127.9 (2 ꢀ CH), 128.7 (2 ꢀ CH), 138.2 (C0) and
169.8 (CO); m/z (EI) 150 (Mþ þ 1, 100%), 106 (90) 91
(20), 77 (6) and 51 (5).
N-Phenethyl-acetamide (12).15 (0.51 g, 51%) as a
white crystalline solid; dH (400 MHz, CDCl3/TMS) 1.93
(3 H, s, CH3), 2.81 (2 H, t, J 7.0, CH2), 3.52 (2 H, m,
CH2), 5.50 (1 H, br s, NH), 7.19 (2 H, m, 2 ꢀ Ar), 7.24 (H,
Copyright # 2007 John Wiley & Sons, Ltd.
J Label Compd Radiopharm 2007; 50: 189–196
DOI: 10.1002.jlcr