The Journal of Organic Chemistry
Page 4 of 7
1.32 (s, 9H). 13C NMR (100 MHz, CDCl3) δ 170.7, 153.2, 132.3,
4-methoxy-N-methylbenzamide (4a)17 Purification by chromaꢀ
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127.0, 125.5, 66.9(2C), 48.4, 42.4, 34.8, 31.2. IR (KBr) ν
̃
2955,
tography (petroleum ether/EtOAc = 6:1) afforded 4a as a yellow
liquid (25 mg, 76%); H NMR (400 MHz, CDCl3) δ 7.74 (d, J =
1
1635, 1431, 1109, 835, 747 cmꢀ1. HRMS (ESIꢀTOF) calcd for
C15H21NNaO2 (M + Na+) 270.1470, found 270.1472.
7.7 Hz, 2H), 6.89 (d, J = 7.7 Hz, 2H), 6.40 (bs, 1H), 3.83 (s, 3H),
2.97 (d, J = 2.9 Hz, 3H).13C NMR (100 MHz, CDCl3) δ 167.8,
162.1, 128.6, 127.1, 113.7, 55.3, 26.7.
(4-Methoxyphenyl)(morpholino)methanone (3g)17 Purification
by chromatography (petroleum ether/EtOAc = 6:1) afforded 3g as
a yellow liquid (38 mg, 87%); 1H NMR (400 MHz, CDCl3) δ 7.39
(d, J = 8.6 Hz, 2H), 6.92 (d, J = 7.9 Hz, 2H), 3.84 (s, 3H), 3.70ꢀ
3.61 (m, 8H). 13C NMR (100 MHz, CDCl3) δ 170.4, 160.8, 129.1,
127.2, 113.7, 66.8 (2C), 55.3, 48.1, 43.1.
(4-fluorophenyl)(morpholino)methanone (3h) Purification by
chromatography (petroleum ether/EtOAc = 8:1) afforded 3h as a
yellow liquid (21 mg, 50%); 1H NMR (400 MHz, CDCl3) δ 7.45 –
7.40 (m, 2H), 7.14 – 7.08 (m, 2H), 3.96 – 3.38 (m, 8H). 13C NMR
(100 MHz, CDCl3) δ 169.5, 164.7, 162.2, 131.3 (d, J = 3.5 Hz),
N-butyl-4-methoxybenzamide (4b)17 Purification by chromatogꢀ
raphy (petroleum ether/EtOAc = 6:1) afforded 4b as a yellow
1
liquid (33 mg, 80%); H NMR (400 MHz, CDCl3) δ 7.73 (d, J =
8.5 Hz, 2H), 6.90 (d, J = 8.5 Hz, 2H), 6.19 (bs, 1H), 3.84 (s, 3H),
3.45ꢀ3.40 (m, 2H), 1.62ꢀ1.55 (m, 2H), 1.45ꢀ1.35 (m, 2H), 0.95 (t,
J = 7.3 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 167.1, 162.0,
128.6, 127.1, 113.7, 55.4, 39.8, 31.8, 20.2, 13.8.
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N-hexyl-4-methoxybenzamide (4c)17 Purification by chromatogꢀ
raphy (petroleum ether/EtOAc = 6:1) afforded 4c as a yellow
solid (32 mg, 69%), mp: 62−64 °C; 1H NMR (400 MHz, CDCl3) δ
7.72 (d, J = 8.5 Hz, 2H), 6.90 (d, J = 8.3 Hz, 2H), 6.11 (bs, 1H),
3.83 (s, 3H), 3.44ꢀ3.39 (m, 2H), 1.63ꢀ1.55 (m, 2H), 1.38ꢀ1.30 (m,
6H), 0.88 (t, J = 6.5 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ
167.0, 162.0, 128.6, 127.2, 113.7, 55.4, 40.0, 31.5, 29.7, 26.7,
22.5, 14.0.
129.5 (d, J = 8.5 Hz), 115.8, 115.6, 66.9, 48.3, 42.8. IR (KBr) ν
̃
2959, 1637, 1450, 1011, 893, 756 cmꢀ1. HRMS (ESIꢀTOF) calcd
for C11H12NNaO2F (M + Na+) 232.0750, found 232.0744.
(4-chlorophenyl)(morpholino)methanone (3i)17 Purification by
chromatography (petroleum ether/EtOAc = 8:1) afforded 3i as a
1
yellow liquid (28 mg, 63%); H NMR (400 MHz, CDCl3) δ 7.40
(d, J = 8.5 Hz, 2H), 7.35 (d, J = 8.4 Hz, 2H), 3.69ꢀ3.49 (m, 8H).
13C NMR (100 MHz, CDCl3) δ 169.4, 136.1, 133.6, 128.9, 128.7,
66.8(2C), 48.1, 42.6.
4-methoxy-N-phenethylbenzamide (4d)17 Purification by chroꢀ
matography (petroleum ether/EtOAc = 6:1) afforded 4d as a yelꢀ
1
low solid (36 mg, 70%). mp: 117−118 °C; H NMR (400 MHz,
(4-bromophenyl)(morpholino)methanone (3j)17 Purification by
chromatography (petroleum ether/EtOAc = 8:1) afforded 3j as a
yellow solid (30 mg, 56%). mp: 91−92 °C; 1H NMR (400 MHz,
CDCl3) δ 7.56 (d, J = 8.3 Hz, 2H), 7.29 (d, J = 8.4 Hz, 2H), 3.69ꢀ
3.46 (m, 8H). 13C NMR (100 MHz, CDCl3) δ 169.4, 134.1, 131.8,
128.9, 124.3, 66.8(2C), 48.1, 42.8.
CDCl3) δ 7.68 (d, J = 8.8 Hz, 2H), 7.35ꢀ7.31 (m, 2H), 7.27ꢀ7.23
(m, 3H), 6.90 (d, J = 8.8 Hz, 2H), 6.21 (bs, 1H), 3.84 (s, 3H),
3.73ꢀ3.69 (m, 2H), 2.93 (t, J = 6.9 Hz, 2H). 13C NMR (100 MHz,
CDCl3) δ 167.0, 162.1, 139.1, 128.8, 128.7, 128.6, 127.0, 126.5,
113.7, 55.4, 41.1, 35.8. IR (KBr) ν̃ 2931, 1637, 1456, 1028, 843,
750 cmꢀ1. HRMS (ESIꢀTOF) calcd for C16H17NNaO2 (M + Na+)
278.1157, found 278.1157.
(4-iodophenyl)(morpholino)methanone (3k)17 Purification by
chromatography (petroleum ether/EtOAc = 8:1) afforded 3k as a
yellow solid (29 mg, 45%). mp: 123−125 °C; 1H NMR (400 MHz,
CDCl3) δ 7.78 – 7.73 (m, 2H), 7.17 – 7.11 (m, 2H), 3.84 – 3.36
(m, 8H); 13C NMR (100 MHz, CDCl3) 169.5, 137.7, 134.7, 128.8,
96.1, 66.8, 48.1, 42.5.
N-benzyl-4-methoxybenzamide (4e) Purification by chromatogꢀ
raphy (petroleum ether/EtOAc = 6:1) afforded 4e as a yellow
solid (34 mg, 70%). mp: 123−126 °C; 1H NMR (400 MHz, CDCl3)
δ 7.76 (d, J = 8.8 Hz, 2H), 7.36 – 7.28 (m, 5H), 6.91 (d, J = 8.8
Hz, 2H), 6.40 (bs, 1H), 4.62 (d, J = 5.7 Hz, 2H), 3.84 (s, 3H). 13
C
(3,5-dimethylphenyl)(morpholino)methanone (3l)17 Purificaꢀ
tion by chromatography (petroleum ether/EtOAc = 8:1) afforded
3l as a colorless oil (33 mg, 75%); 1H NMR (400 MHz, CDCl3) δ
7.04 (s, 1H), 6.99 (s, 2H), 3.88 – 3.37 (m, 8H), 2.33 (s, 6H). 13C
NMR (100 MHz, CDCl3) δ 170.8, 138.3, 135.3, 131.4, 124.6, 66.9,
48.3, 42.6, 21.2.
NMR (100 MHz, CDCl3) δ 166.9, 162.3, 138.4, 128.8, 128.8,
127.9, 127.6, 126.7, 113.8, 55.4, 44.1. IR (KBr) ν̃ 2920, 1634,
1441, 1033, 845, 726 cmꢀ1. HRMS (ESIꢀTOF) calcd for
C15H15NNaO2 (M + Na+) 264.1000, found 264.1005.
4-methoxy-N-(4-methoxybenzyl)benzamide (4f) Purification by
chromatography (petroleum ether/EtOAc = 6:1) afforded 4e as a
yellow solid (39 mg, 72%), mp: 160−162 °C; 1H NMR (400 MHz,
CDCl3) δ 7.74 (d, J = 8.8 Hz, 2H), 7.26 (d, J = 8.5 Hz, 2H), 6.90ꢀ
6.85 (m, 4H), 6.45 (bs, 1H), 4.53 (d, J = 5.5 Hz, 2H), 3.82 (s, 3H),
3.78 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 166.8, 162.2, 159.1,
130.5, 129.3, 128.8, 126.7, 114.1, 113.7, 55.4, 55.3, 43.5. IR
(3,4-dimethylphenyl)(morpholino)methanone (3m) Purification
by chromatography (petroleum ether/EtOAc = 8:1) afforded 3m
as a yellow liquid (40 mg, 91%); 1H NMR (400 MHz, CDCl3) δ
7.12 (s, 1H), 7.09ꢀ7.03 (m, 2H), 3.61ꢀ3.42 (m, 8H), 2.21ꢀ2.18 (m,
6H). 13C NMR (100 MHz, CDCl3) δ 170.8, 138.7, 137.0, 132.8,
129.6, 128.4, 124.5, 66.9(2C), 48.3, 42.6, 19.7, 19.7. IR (KBr) ν
2921, 1636, 1428, 1029, 822, 761 cmꢀ1. HRMS (ESIꢀTOF) calcd
for C13H17NNaO2 (M + Na+) 242.1157, found 242.1158.
̃
(KBr) ν̃
2958, 1632, 1440, 1028, 846, 772 cmꢀ1. HRMS (ESIꢀTOF)
calcd for C16H17NNaO3 (M + Na+) 294.1106, found 294.1109.
N-(4-fluorobenzyl)-4-methoxybenzamide (4g) Purification by
chromatography (petroleum ether/EtOAc = 6:1) afforded 4e as a
yellow solid (46 mg, 89%), mp: 134−136 °C; 1H NMR (400 MHz,
CDCl3) δ 7.75 (d, J = 8.7 Hz, 2H), 7.32ꢀ7.49 (m, 2H), 7.03ꢀ6.99
(m, 2H), 6.90 (d, J = 8.7 Hz, 2H), 6.47 (bs, 1H), 4.58 (d, J = 5.7
Hz, 2H), 3.84 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 166.9, 162.3,
162.2 (d, JCꢀF = 245.0), 134.3 (d, JCꢀF = 3.0), 129.5 (d, J CꢀF= 8.0),
(2,4-dimethylphenyl)(morpholino)methanone (3n) Purification
by chromatography (petroleum ether/EtOAc = 8:1) afforded 3n as
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a yellow liquid (28 mg, 65%); H NMR (400 MHz, CDCl3) δ
7.06ꢀ7.01 (m, 3H), 3.81ꢀ3.76 (m, 4H), 3.60ꢀ3.52 (m, 2H), 3.28ꢀ
3.21 (m, 2H), 2.32 (s, 3H), 2.28 (s, 3H). 13C NMR (100 MHz,
CDCl3) δ 170.4, 138.9, 134.1, 132.7, 131.2, 126.6, 125,9,
67.0(2C), 47.3, 42.0, 21.2, 19.0. IR (KBr) ν
̃
2961, 1635, 1429,
128.8, 126.5, 115.56 (d, JCꢀF = 22.0), 113.8, 55.4, 43.3. IR (KBr) ν
2931, 1632, 1423, 1027, 843, 776 cmꢀ1. HRMS (ESIꢀTOF) calcd
for C15H14NNaO2 F(M + Na+) 282.0906, found 282.0903.
̃
1020, 822, 761 cmꢀ1. HRMS (ESIꢀTOF) calcd for C13H17NNaO2
(M + Na+) 242.1157, found 242.1157.
morpholino(naphthalen-2-yl)methanone (3o) Purification by
chromatography (petroleum ether/EtOAc = 8:1) afforded 3n as a
N-cyclopentyl-4-methoxybenzamide (4h)17 Purification by
chromatography (petroleum ether/EtOAc = 6:1) afforded 4h as a
yellow solid (35 mg, 80%). mp: 150−152 °C; 1H NMR (400 MHz,
CDCl3) δ 7.71 (d, J = 8.8 Hz, 2H), 6.90 (d, J = 8.8 Hz, 2H), 6.00
(bs, 1H), 4.43ꢀ4.34 (m, 1H), 3.84 (s, 3H), 2.12ꢀ2.04 (m, 2H), 1.72ꢀ
1.62 (m, 4H), 1.52ꢀ1.44 (m, 2H). 13C NMR (100 MHz, CDCl3) δ
166.7, 162.0, 128.6, 127.3, 113.7, 55.4, 51.6, 33.3, 23.8.
1
red solid (40 mg, 83%), mp: 101ꢀ103 °C ; H NMR (400 MHz,
CDCl3) δ 7.91ꢀ7.89 (m, 4H), 7.55ꢀ7.48 (m, 3H), 3.93ꢀ3.44 (s, 8H).
13C NMR (100 MHz, CDCl3) δ 170.5, 133.8, 132.7, 132.6, 128.5,
128.4, 127.8, 127.2, 127.1, 126.8, 124.2, 67.0(2C), 48.3, 42.7. IR
(KBr) ν
̃
2964, 1621, 1427, 1066, 839, 753 cmꢀ1. HRMS (ESIꢀTOF)
calcd for C15H15NNaO2 (M + Na+) 264.1000, found 264.0999.
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