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Organic & Biomolecular Chemistry
4/1), Rf = 0.51, to afford a pale yellow oil in 76% yield; 1H NMR
(3-Chlorophenyl)(piperidin-1-yl)methanone (4i).20 Prepared
(400 MHz, CDCl3) δ 0.74 (t, J = 7.2 Hz, 2H), 0.98 (t, J = 7.4 Hz, according to the general procedure. The product was purified
2H), 1.1 (q, J = 7.4 Hz, 2H), 1.37–1.47 (m, 4H), 1.6–1.7 (m, 2H), by flash chromatography on silica gel (v/v petroleum ether–
2.28 (s, 3H), 3.04 (t, J = 7.4 Hz, 2H), 3.3 (br s, 2H), 3.65 (br s, AcOEt = 3.8/1.2), Rf = 0.45, to afford a yellow oil in 58% yield;
2H), 7.12–7.25 (m, 4H); 13C NMR (100 MHz, CDCl3) δ 13.7, 1H NMR (400 MHz, CDCl3) δ 1.55 (br s, 4H), 1.71 (br s, 4H),
14.1, 19.1, 19.9, 20.6, 29.8, 30.8, 44.2, 48.2, 125.8, 125.9, 128.6, 3.35 (br s, 2H), 3.72 (br s, 2H), 7.27–7.40 (m, 4H); 13C NMR
130.4, 134.1, 137.4, 171.4; IR (neat) ν = 2958, 2931, 2869, 1633, (100 MHz, CDCl3) δ 24.5, 25.6, 26.6, 43.2, 48.8, 124.9, 127.0,
1463, 1423, 1376, 1301, 1261, 746. HRMS (EI) ([M+]) Calcd for 129.5, 129.8, 134.5, 138.2, 168.7; IR (neat) ν = 2931, 2856, 1631,
C16H25NO: 247.1936, Found: 247.1933.
1566, 1439, 1280, 800, 739.
Morpholino(o-tolyl)methanone (4d).18 Prepared according
N-Benzyl-N-methylbenzamide (4j).7h Prepared according to
to the general procedure. The product was purified by flash the general procedure. The product was purified by flash
chromatography on silica gel (v/v petroleum ether–AcOEt = chromatography on silica gel (v/v petroleum ether–Et2O = 3.5/
1
2.5/2.5), Rf = 0.31, to afford a yellow oil in 86% yield; H NMR 1.5), Rf = 0.26, to afford a pale yellow oil in 79% yield; 1H NMR
(400 MHz, CDCl3) δ 2.32 (s, 3H), 3.24 (br d, J = 4.5 Hz, 2H), (400 MHz, CDCl3) δ 2.89 (br s, 1.5H), 3.06 (br s, 1.5H), 4.54 (br
3.57 (br t, J = 4.5 Hz, 2H), 3.76–3.84 (br m, 4H), 7.14–7.3 (m, s, 1H), 4.79 (br s, 1H), 7.20–7.47 (m, 10H); 13C NMR (100 MHz,
4H); 13C NMR (100 MHz, CDCl3) δ 19.1, 41.9, 47.3, 66.9, 67.0, CDCl3) δ 33.2, 37.1, 50.8, 55.2, 126.8, 127.0, 127.6, 127.9, 128.2,
125.8, 126.0, 129.1, 130.5, 134.2, 135.6, 170.1; IR (neat) ν = 128.4, 128.8, 129.6, 136.3, 136.6, 137.1, 170.8, 171.6; IR (neat)
3054, 2983, 2923, 2859, 1633, 1431, 1265, 1157, 704.
Morpholino(4-nitrophenyl)methanone
(4e).18 Prepared
ν = 2921, 1631, 1450, 1400, 1265, 1070, 1026, 698.
N,N-Dibenzylthiophene-2-carboxamide
(4k).13 Prepared
according to the general procedure. The product was purified according to the general procedure. The product was purified
by flash chromatography on silica gel (v/v petroleum ether– by flash chromatography on silica gel (v/v petroleum ether–
AcOEt = 2.5/2.5), Rf = 0.23, to afford a white solid in 77% yield Et2O = 3/2), Rf = 0.58, to afford a white solid in 98% yield (m.p.
1
(m.p. 98–101 °C); 1H NMR (400 MHz, CDCl3) δ 3.41–3.82 (br 47–50 °C); H NMR (400 MHz, CDCl3) δ 4.75 (s, 4H), 6.98 (dd,
m, 8H), 7.61 (d, J = 8.8 Hz, 2H), 8.31 (d, J = 8.8 Hz, 2H); 13C J = 3.7 Hz, J = 5.1 Hz, 1H), 7.30–7.42 (m, 11H), 7.47 (dd, J = 1.2
NMR (100 MHz, CDCl3) δ 42.6, 48.0, 66.8, 124.0, 128.2, 141.4, Hz, J = 5.1 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 50.1, 126.9,
148.5, 168.1; IR (neat) ν = 2922, 2856, 1637, 1523, 1435, 1352, 127.6, 128.6, 128.8, 129.3, 136.6, 137.7, 165.1. IR (neat) ν =
1279, 1113, 1012, 895, 839, 735.
3062, 3004, 2978, 2954, 2914, 1611, 1583, 1519, 1494, 1453,
(4-Fluorophenyl)(piperidin-1-yl)methanone (4f).19 Prepared 1422, 1364, 1347, 1306, 1250, 1078, 889.
according to the general procedure. The product was purified
Piperidin-1-yl(o-tolyl)methanone (4l).12 Prepared according
by flash chromatography on silica gel (v/v petroleum ether– to the general procedure. The product was purified by flash
AcOEt = 3/2), Rf = 0.2, to afford a pale yellow oil in 70% yield; chromatography on silica gel (v/v petroleum ether–AcOEt =
1
1H NMR (400 MHz, CDCl3) δ 1.57 (br s, 2H), 1.71 (br s, 4H), 3.5/1.5), Rf = 0.38, to afford a pale yellow oil in 85% yield; H
3.37 (br s, 2H), 3.71 (br s, 2H), 7.08–7.12 (m, 2H), 7.39–7.43 NMR (400 MHz, CDCl3) δ 1.46 (s, 2H), 1.66 (s, 4H), 2.31 (s,
(m, 2H), 13C NMR (100 MHz, CDCl3) δ 24.6, 25.7, 26.6, 43.2, 3H), 3.17 (d, J = 4.1 Hz, 2H), 3.71 (br s, 1H), 3.79 (br s, 1H),
48.9, 115.3, 115.6, 129.0, 129.1, 132.4, 132.5, 161.9, 164.4, 7.21 (m, 4H); 13C NMR (100 MHz, CDCl3) δ 18.9, 24.5, 25.7,
169.4; IR (neat) ν = 2942, 1628, 1442, 1265, 1157, 1004, 26.5, 42.3, 47.8, 125.6, 125.8, 128.5, 130.2, 134.0, 136.7, 169.8;
847, 739.
IR (neat) ν = 3049, 2938, 2857, 1627, 1444, 1350, 1288, 1271,
(4-Chlorophenyl)(piperidin-1-yl)methanone (4g).19 Prepared 1240, 1129, 1097, 1027, 1000, 733, 700, 665.
according to the general procedure. The product was purified
N-Benzylthiophene-2-carboxamide (4m).21 Prepared accord-
by flash chromatography on silica gel (v/v petroleum ether– ing to the general procedure. The product was purified by
Et2O = 3/2), Rf = 0.2, to afford a white solid in 69% yield flash chromatography on silica gel (v/v petroleum ether–Et2O =
1
1
(m.p. 59–61 °C); H NMR (400 MHz, CDCl3) δ 1.54 (br, s, 2H), 2.5/2.5), Rf = 0.35, to afford a pale yellow oil in 63% yield; H
1.70 (br s, 4H), 3.35 (br s, 2H), 3.71 (br s, 2H), 7.34–7.41 (m, NMR (400 MHz, CDCl3) δ 4.64 (d, J = 5.7 Hz, 2H), 6.35 (br s,
4H); 13C NMR (100 MHz, CDCl3) δ 24.5, 25.6, 26.6, 43.2, 48.9, 1H), 7.09 (dd, J = 3.7 Hz, J = 5.1 Hz, 1H), 7.31–7.35 (m, 1H),
128.4, 128.7, 134.8, 135.4, 169.2; IR (neat) ν = 2937, 1629, 1440, 7.37–7.38 (m, 4H), 7.50 (dd, J = 1.2 Hz, J = 5.1 Hz, 1H), 7.53
1277, 1090, 1003, 737.
(dd, J = 1.1 Hz, J = 2.5 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ
(4-Bromophenyl)(piperidin-1-yl)methanone (4h).7g Prepared 44.0, 127.6, 127.7, 127.9, 128.1, 128.8, 130.0, 138.0, 138.7,
according to the general procedure. The product was purified 161.8; IR (neat) ν = 2922, 1629, 1545, 1421, 1265, 737.
by flash chromatography on silica gel (v/v petroleum ether–
N-Pentylbenzamide (4n).22 Prepared according to the
Et2O = 3/2), Rf = 0.23, to afford a white solid in 80% yield (m.p. general procedure. The product was purified by flash chro-
75–78 °C); 1H NMR (400 MHz, CDCl3) δ 1.54 (br s, 2H), 1.70 matography on silica gel (v/v petroleum ether–Et2O = 2.5/2.5),
(br s, 4H), 3.26 (br s, 2H), 3.71 (br s, 2H), 7.29 (d, J = 8.5 Hz, Rf = 0.51, to afford a pale yellow oil in 92% yield; 1H NMR
2H), 7.55 (d, J = 8.5 Hz, 2H); 13C NMR (100 MHz, CDCl3) (400 MHz, CDCl3) δ 0.94 (t, J = 7.1 Hz, 3H), 1.38 (m, 4H), 1.64
δ 24.5, 25.6, 26.5, 43.3, 48.8, 123.6, 128.6, 131.6, 135.3, 169.3; (t, J = 7.3 Hz, 2H), 3.47 (q, J = 7.2 Hz, 2H), 6.19 (br s, 1H),
IR (neat) ν = 2933, 2854, 1631, 1441, 1277, 1111, 1068, 1001, 7.42–7.53 (m, 3H), 7.78 (m, 2H); 13C NMR (100 MHz, CDCl3)
833, 733.
δ 14.0, 22.4, 29.1, 29.4, 40.1, 126.8, 128.5, 131.3, 134.9, 167.5;
3806 | Org. Biomol. Chem., 2013, 11, 3803–3807
This journal is © The Royal Society of Chemistry 2013