10398
K. Singh, K. Singh / Tetrahedron 65 (2009) 10395–10399
dH (300 MHz, CDCl3) 5.40 (1H, br s, exchanged with D2O, NH), 3.24
(2H, q, J 7.2 Hz, CH2NH), 1.97 (3H, s, COCH3), 1.43–1.53 (2H, m,
CH2CH2NH), 1.28–1.38 (2H, m, CH2CH3(CH2)2), 0.92 (3H, t, J 6.9 Hz,
CH3CH2); dC (75 MHz, CDCl3) 170.1, 39.3, 31.5, 23.1, 19.9, 13.6; m/z
116 (Mþ1).
(3H, t, J 3.6 Hz, CH3CH2); dC (75 MHz, CDCl3) 173.7, 148.9, 147.0,
131.3, 120.5, 111.8, 111.3, 55.8, 40.5, 35.1, 29.6, 9.8; m/z 260 (Mþ23).
4.3.12. N-[2-(1H-Indol-3-yl)ethyl]propionamide (20). Viscous liq-
uid; [Found: C, 72.13; H, 7.50; N, 12.62. C13H16N2O requires C, 72.22;
H, 7.40; N, 12.96%]; Rf (40% EtOAc/hexane) 0.16; nmax (CHCl3) 3010,
4.3.5. N-sec-Butylacetamide (13). Viscous liquid; [Found: C, 62.35;
H, 11.37; N, 12.24. C6H13NO requires C, 62.60; H, 11.30; N, 12.17%]; Rf
1710, 1210, 740 cmꢁ1
; dH (300 MHz, CDCl3) 8.20 (1H, br s, ex-
changed with D2O, NH), 7.10–7.62 (4H, m, ArH), 7.03 (1H, s, 1H-
indole), 5.53 (1H, br s, exchanged with D2O, NH), 3.60 (2H, q, J
6.6 Hz, CH2NH), 2.97 (2H, t, J 6.3 Hz, CH2 indole), 2.11 (2H, q, J 7.5 Hz,
COCH2CH3), 1.10 (3H, t, J 7.5 Hz, CH3CH2); dC (75 MHz, CDCl3) 173.2,
122.0, 119.3, 118.6, 112.8, 111.2, 39.7, 29.7, 25.2, 9.7; m/z 217 (Mþ1).
(30% EtOAc/hexane) 0.6; nmax (CHCl3) 2990, 1670, 1225 cmꢁ1
; dH
(300 MHz, CDCl3) 5.23 (1H, br s, exchanged with D2O, NH), 3.85–
3.95 (1H, m, CHNH), 1.98 (3H, s, COCH3), 1.40–1.47 (2H, m, CH2CH3),
1.11 (3H, d, J 6.6 Hz, CH3CH), 0.90 (3H, t, J 7.2 Hz, CH3CH2); dC
(75 MHz, CDCl3) 169.4, 46.6, 29.6, 23.4, 20.3, 10.2; m/z 138 (Mþ23).
4.3.13. DL-3-(1H-Indol-3-yl)-2-propionylaminopropionic acid methyl
ester (21). Colourless solid; [Found: C, 65.41; H, 6.46; N, 10.52.
C15H18N2O3 requires C, 65.69; H, 6.56; N, 10.21%]; Rf (40% EtOAc/
hexane) 0.2; mp: 136 ꢀC (DCM/hexane); nmax (CHCl3) 2900, 1700,
4.3.6. N-Heptylacetamide (14). Viscous liquid; [Found: C, 68.66; H,
12.34; N, 9.17. C9H19NO requires C, 68.78; H,12.10; N, 8.91%]; Rf (35%
EtOAc/hexane) 0.5; nmax (CHCl3) 2950, 1630, 1230 cmꢁ1
; dH
(300 MHz, CDCl3) 5.47 (1H, br s, exchanged with D2O, NH), 3.23
(2H, q, J 7.2 Hz, CH2NH), 1.97 (3H, s, COCH3), 1.49–1.59 (2H, m,
CH2CH2NH), 1.28–1.30 (8H, m, (CH2)4), 0.88 (3H, t, J 6.9 Hz,
CH3CH2); dC (75 MHz, CDCl3) 169.1, 39.6, 31.7, 29.5, 28.9, 26.8, 23.3,
22.5, 14.0; m/z 180 (Mþ23).
1210, 750 cmꢁ1
; dH (300 MHz, CDCl3) 8.21 (1H, br s, exchanged with
D2O, NH), 6.98–7.54 (4H, m, ArH), 6.97 (1H, d, J 2.4 Hz, 1H-indole),
5.96 (1H, br s, exchanged with D2O, NH,), 4.93–5.00 (1H, m,
CH(CH2)NH), 3.70 (3H, s, COOCH3), 3.31–3.40 (2H, m,
CH2CHCOOCH3), 2.18 (2H, q, J 7.8 Hz, COCH2CH3),1.11 (3H, t, J 7.5 Hz,
CH3CH2); dC (75 MHz, CDCl3) 173.4, 172.5, 136.0, 127.7, 122.6, 122.1,
119.6, 118.5, 111.2, 110.0, 52.8, 52.3, 29.5, 27.5, 9.5; m/z 297 (Mþ23).
4.3.7. N-(2-Hydroxyphenyl)-propionamide (15). Brownish solid;
[Found: C, 65.20; H, 6.30; N, 8.10. C9H11NO2 requires C, 65.45; H,
6.66; N, 8.48%]; Rf (40% EtOAc/hexane) 0.7; mp: 62–64 ꢀC (DCM/
4.3.14.
D-3-(1H-Indol-3-yl)-2-propionylaminopropionic acid methyl
hexane); nmax (CHCl3) 3020, 1698, 1215, 760 cmꢁ1
;
dH (300 MHz,
ester (22). Viscous liquid; [Found: C, 65.30; H, 6.20; N, 9.90.
CDCl3) 8.80 (1H, br s, exchanged with D2O, OH), 7.45 (1H, br s,
exchanged with D2O, NH), 6.83–7.15 (5H, m, ArH), 2.50 (2H, q, J
7.5 Hz, COCH2CH3), 1.29 (3H, t, J 7.5 Hz, CH3CH2); dC (75 MHz, CDCl3)
174.1, 148.6, 127.0, 122.0, 120.4, 119.7, 30.0, 9.8; m/z 165 (Mþ).
C15H18N2O3 requires C, 65.69; H, 6.56; N, 10.21%]; Rf (40% EtOAc/
20
hexane) 0.2; [
a
;
]
ꢁ4.00 (c 0.5, CHCl3); nmax (CHCl3) 3440, 1700,
D
1215, 757 cmꢁ1
dH (300 MHz, CDCl3) 8.11 (1H, br s, exchanged with
D2O, NH), 7.07–7.52 (4H, m, ArH), 6.95 (1H, d, J 2.4 Hz, 1H-indole),
6.05 (1H, br s, exchanged with D2O, NH), 4.92–4.98 (1H, m,
CH(CH2)NH), 3.68 (3H, s, COOCH3), 3.30–3.39 (2H, m,
CH2CHCOOCH3), 2.16 (2H, q, J 7.5 Hz, COCH2CH3), 1.09 (3H, t, J
7.5 Hz, CH3CH2); dC (75 MHz, CDCl3) 173.4, 172.5, 136.0, 122.6, 122.1,
119.6, 118.5, 111.2, 110.0, 52.8, 52.3, 29.5, 27.5, 9.5; m/z 297 (Mþ23).
4.3.8. N-(2-Mercaptophenyl)propionamide (16)4. Colourless solid;
[Found: C, 59.30; H, 6.30; N, 7.52; S, 17.40. C9H11NOS requires C,
59.66; H, 6.07; N, 7.73; S, 17.67%]; Rf (40% EtOAc/hexane) 0.5; mp:
105 ꢀC (DCM/hexane); nmax (CHCl3) 3415, 3300, 1610 cmꢁ1
; dH
(300 MHz, CDCl3) 8.40 (1H, d, J 8.1 Hz, ArH), 7.98 (1H, br s, exchanged
with D2O, NH,), 6.97–7.43 (3H, m, ArH), 2.19 (2H, q, J 7.5 Hz,
COCH2CH3), 1.14 (3H, t, J 7.5 Hz, CH3CH2); dC (75 MHz, CDCl3) 174.0,
155.2, 139.9, 136.4, 132.1, 123.0, 120.8, 29.9, 9.4; m/z 180 (Mꢁ1).
4.3.15. L-3-(1H-Indol-3-yl)-2-propionylaminopropionic acid methyl
ester (23). Viscous liquid; [Found: C, 65.30; H, 6.30; N, 9.90.
C15H18N2O3 requires C, 65.69; H, 6.56; N, 10.21%]; Rf (40% EtOAc/
20
hexane) 0.2; [
a
]
þ4.00 (c 0.5, CHCl3); nmax (CHCl3) 3320, 1710,
D
4.3.9. N-(2-Propionylaminophenyl)propionamide (17)4. Colourless
solid; [Found: C, 65.80; H, 7.50; N, 12.40. C12H16N2O2 requires C,
65.45; H, 7.27; N, 12.72%]; Rf (40% EtOAc/hexane) 0.3; mp:
1210, 755 cmꢁ1
; dH (300 MHz, CDCl3) 8.32 (1H, br s, exchanged with
D2O, NH), 7.00–7.45 (4H, m, ArH), 6.95 (1H, d, J 2.4 Hz, 1H-indole),
5.94 (1H, br s, exchanged with D2O, NH), 4.85–4.91 (1H, m,
CH(CH2)NH), 3.61 (3H, s, COOCH3), 3.23–3.28 (2H, m,
CH2CHCOOCH3), 2.09 (2H, q, J 7.5 Hz, COCH2CH3), 0.99 (3H, t, J
7.5 Hz, CH3CH2); dC (75 MHz, CDCl3) 173.4, 172.5, 136.0, 122.6, 122.1,
119.6, 118.5, 111.2, 110.0, 52.8, 52.3, 29.5, 27.5, 9.5; m/z 297 (Mþ23).
115–118 ꢀC (DCM/hexane); nmax (CHCl3) 3300, 1665, 760 cmꢁ1
; dH
(300 MHz, CDCl3) 8.17 (2H, br s, exchanged with D2O, NH),
7.06–7.36 (4H, m, ArH), 2.37 (4H, q, J 7.5 Hz, 2ꢂCOCH2CH3), 1.22
(6H, t, J 7.5 Hz, 2ꢂCH3CH2); dC (75 MHz, CDCl3) 173.4, 137.0, 130.5,
126.0, 125.5, 30.1, 9.7; m/z 243 (Mþ23).
4.3.16. N,N-Diethylacetamide (24)3h. Viscous liquid; [Found: C,
62.30; H, 10.90; N, 11.97. C6H13NO requires C, 62.60; H, 11.30; N,
12.17%]; Rf (30% EtOAc/hexane) 0.6; nmax (CHCl3) 3020, 1730,
4.3.10. N-Phenethylpropionamide (18). Colourless solid; [Found: C,
74.30; H, 8.20; N, 7.50. C11H15NO requires C, 74.57; H, 8.47; N, 7.90%];
Rf (40% EtOAc/hexane) 0.5; mp: 52–54 ꢀC (DCM/hexane); nmax
1215 cmꢁ1
;
dH (300 MHz, CDCl3) 3.34 (4H, q, J 7.2 Hz, 2ꢂCH2CH3),
(CHCl3) 3020, 1700, 1655, 1215 cmꢁ1
;
dH (300 MHz, CDCl3) 7.17–7.34
2.09 (3H, s, COCH3), 1.18 (6H, t, J 7.2 Hz, 2ꢂCH3CH2); dC (75 MHz,
CDCl3) 169.9, 42.86, 40.0, 21.2, 14.0, 13.0; m/z 138 (Mþ23).
(5H, m, ArH), 5.42 (1H, br s, exchanged with D2O, NH), 3.52 (2H, q, J
6.9 Hz, CH2NH), 2.81 (2H, t, J 6.9 Hz, CH2Ph), 2.15 (2H, q, J 7.8 Hz,
COCH2CH3), 1.12 (3H, t, J 7.5 Hz, CH3CH2); dC (75 MHz, CDCl3) 173.0,
145.9, 128.7, 127.9, 126.5, 60.0, 55.8, 18.8, 14.1; m/z 178 (Mþ1).
4.3.17. 1-Morpholin-4-yl-ethanone (25)3h. Viscous liquid; [Found:
C, 55.61; H, 8.40; N, 10.78. C6H11NO2 requires C, 55.81; H, 8.53; N,
10.85%]; Rf (40% EtOAc/hexane) 0.5; nmax (CHCl3) 3350, 2750, 1700,
4.3.11. N-[2-(3,4-Dimethoxyphenyl)ethyl]propionamide (19). Light
brown solid; [Found: C, 65.90; H, 7.80; N, 5.50. C13H19NO3 requires
C, 65.82; H, 8.01; N, 5.90%]; Rf (50% EtOAc/hexane) 0.2; mp: 42–
1655, 1240 cmꢁ1
;
dH (300 MHz, CDCl3) 3.61–3.70 (6H, m, 2ꢂCH2O
and CH2NCOCH3), 3.46 (2H, t, J 4.8 Hz, CH2NCOCH3), 2.09 (3H, s,
COCH3); dC (75 MHz, CDCl3) 169.1, 66.7, 66.5, 46.5, 41.7, 21.0; m/z
152 (Mþ23).
44 ꢀC (DCM/hexane); nmax (CHCl3) 3020, 1700, 1210, 760 cmꢁ1
; dH
(300 MHz, CDCl3) 6.70–6.81 (3H, m, ArH), 5.72 (1H, br s, exchanged
with D2O, NH), 3.85 (6H, s, 2ꢂOCH3), 3.47 (2H, q, J 6.9 Hz, CH2NH),
2.75 (2H, t, J 6.9 Hz, CH2Ph), 2.16 (2H, q, J 7.5 Hz, COCH2CH3), 1.13
4.3.18. 1-Piperidin-1-yl-ethanone (26)3h. Viscous liquid; [Found: C,
66.01; H, 9.90; N, 10.80. C7H13NO requires C, 66.14; H, 10.24; N,