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Surya Srinivas Kotha et al.
2925, 2854, 1634, 1432, 1276, 1091, 1024, 849 cmÀ1; HR-MS:
m/z=224.0838 [M+H]+, calcd. for C12H15ONCl: 224.0837.
(Piperidin-1-yl)phenylmethanone (3f): Yield: 67%; light
3.68 (bs, 2H), 3.29 (bs, 2H), 1.65 (s, 4H), 1.49 (bs, 2H);
13C NMR (100 MHz, CDCl3): d=169.3, 166.4, 136.8, 131.3,
130.5, 130.4, 128.7, 127.9, 52.3, 48.8, 43.3, 26.5, 25.6, 24.5;
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brown oil; Rf =0.43 (30% ethyl acetate in hexane); H NMR
FT-IR: n=2938, 2857, 1725, 1631, 1438, 1298, 1257 cmÀ1
;
(400 MHz, CDCl3): d=7.39–7.33 (s, 5H), 3.81–3.55 (s, 2H),
3.49–3.19 (bs, 2H), 1.71–1.45 (m, 6H); 13C NMR (100 MHz,
CDCl3): d=170.4, 136.6, 129.4, 128.4, 126.8, 48.8, 43.2, 26.6,
25.7, 24.7; FT-IR: n=2934, 2858, 1716, 1625, 1442, 1278,
1115, 1003 cmÀ1; HR-MS: m/z=190.1228 [M+H]+, calcd.
for C12H16ON: 190.1226.
(4-Ethoxyphenyl)(piperidin-1-yl)methanone (3g): Yield:
67%; light orange oil; Rf =0.49 (50% ethyl acetate in
hexane); 1H NMR (400 MHz, CDCl3): d=7.37–7.31 (m,
2H), 6.91–6.84 (m, 2H), 4.04 (q, J=6.8 Hz, 2H), 3.81–3.22
(bs, 4H), 1.72–1.47 (m, 6H), 1.41 (t, J=7.2 Hz, 3H);
13C NMR (100 MHz, CDCl3): d=170.6, 160.1, 129.1, 128.4,
114.3, 63.7, 53.6, 29.8, 29.5, 26.3, 24.8, 14.9; FT-IR: n=2931,
2856, 1609, 1511, 1432, 1248, 1174, 1115, 1043 cmÀ1; HR-MS:
m/z=234.1489 [M+H]+, calcd. for C14H20O2N: 234.1489.
HR-MS: m/z=248.1284 [M+H]+, calcd. for C14H18O3N:
248.1281.
4-(Piperidine-1-carbonyl)benzonitrile (3m): Yield: 66%;
orange sticky oil; Rf =0.46 (50% ethyl acetate in hexane);
1H NMR (400 MHz, CDCl3): d=7.68 (d, J=8.4 Hz, 2H),
7.46 (d, J=8.4 Hz, 2H), 3.69 (brs, 2H), 3.26 (brs, 2H), 3.26
(brs, 2H), 1.73–1.43(m, 2H); 13C NMR (100 MHz, CDCl3):
d=168.3, 141.0, 132.5, 127.6, 118.2, 113.3, 48.7, 43.3, 26.6,
25.6, 24.5; FT-IR: n=2942, 2860, 2251, 1624, 1109, 848 cmÀ1
;
HR-MS: m/z=215.1177 [M+H]+, calcd. for C13H15ON2:
215.1179.
3-(Piperidine-1-carbonyl)benzonitrile (3n): Yield: 66%;
orange sticky oil; Rf =0.46 (50% ethyl acetate in hexane);
1H NMR (400 MHz, CDCl3): d=7.68 (d, J=8.0 Hz, 2H),
7.62 (d, J=7.2 Hz, 1H), 7.53 (t, J=7.2 Hz, 1H), 3.70 (brs,
2H), 3.30 (brs, 2H), 1.77–1.48 (m, 6H); 13C NMR
(100 MHz, CDCl3): d=168.0, 137.8, 133.0, 130.5, 129.6,
118.2, 113.0, 49.0, 43.5, 26.6, 25.6, 24.5; FT-IR: n=2947,
2865, 2247, 1620, 1104, 845 cmÀ1; HR-MS: m/z=215.1176
[M+H]+, calcd. for C13H15ON2: 215.1179.
4-(Morpholine-4-carbonyl)benzonitrile (3o): Yield: 66%;
orange sticky oil; Rf =0.32 (50% ethyl acetate in hexane);
1H NMR (400 MHz, CDCl3): d=7.70 (d, J=8.4 Hz, 2H),
7.49 (d, J=8.4 Hz, 2H), 3.97–3.15 (m, 8H); 13C NMR
(100 MHz, CDCl3): d=168.4, 139.7, 132.6, 127.9, 118.0,
113.8, 66.8, 48.1, 42.7; FT-IR: n=2924, 2342, 2249, 1654,
1609, 1178, 756 cmÀ1; HR-MS: m/z=217.0972 [M+H]+,
calcd. for C12H13O2N2: 217.0977.
(3,5-Dimethoxyphenyl)(piperidin-1-yl)methanone
(3h):
Yield: 70%; orange sticky oil; Rf =0.50 (50% ethyl acetate
in hexane); 1H NMR (400 MHz, CDCl3): d=6.49 (d, J=
2 Hz, 2H), 6.46 (t, J=2 Hz, 1H), 3.78 (s, 6H), 3.73–3.62 (bs,
2H), 3.43–3.21 (bs, 2H), 1.71–1.45 (m, 6H), 1.5 (s, 2H);
13C NMR (100 MHz, CDCl3): d=170.0, 160.9, 138.5, 104.7,
101.5, 55.6, 48.8, 43.2, 26.7, 25.7, 24.7; FT-IR: n=2927, 2853,
1596, 1457, 1428, 1156, 1060 cmÀ1; HR-MS: m/z=250.1438
[M+H]+, calcd, for C14H20O3N: 250.1438.
(3-Methoxyphenyl)(piperidin-1-yl)methanone (3i): Yield:
63%; pale orange liquid; Rf =0.51 (50% ethyl acetate in
hexane); 1H NMR (400 MHz, CDCl3): d=7.34–7.28 (m,
1H), 7.20 (dd, J1 =8 Hz, J2 =1.6 Hz, 1H), 6.89 (d, J=8.4 Hz,
1H) 6.96 (dt, J1 =7.6 Hz, J2 =0.8 Hz, 1H), 3.81 (s, 3H),
3.78–3.63(m, 2H), 3.21–3.12 (m, 2H), 1.69–1.59 (m, 4H),
1.25 (s, 2H); 13C NMR (100 MHz, CDCl3): d=167.8, 155.4,
130.1, 127.8, 126.6, 120.9, 111.0. 55.6, 48.0, 42.6, 29.8, 26.5,
25.8, 24.7; FT-IR: n=2923, 2360, 1594, 1421, 1031 cmÀ1; HR-
MS: m/z=220.1329 [M+H]+, calcd. for C13H18NO2:
220.1338.
Methyl 4-(piperidine-1-carbonyl)benzoate (3j): Yield:
66%; orange sticky oil; Rf =0.55 (50% ethyl acetate in
hexane); 1H NMR (400 MHz, CDCl3): d=8.06 (d, J=
7.6 Hz, 2H), 7.42 (d, J=7.6 Hz, 2H), 4.37 (qd, J1 =7.2 Hz,
J2 =0.8 Hz, 2H), 3.69 (s, 2H), 3.27 (s, 2H), 1.66 (s, 4H), 1.49
(bs, 2H); 13C NMR (100 MHz, CDCl3): d=169.4, 166.0,
140.7, 131.3, 129.8, 126.8, 61.3, 48.7, 43.2, 26.6, 25.7, 24.6,
14.4; FT-IR: n=2978, 2857, 1719, 1632, 1510, 1274,
1107 cmÀ1; HR-MS: m/z=262.1442 [M+H]+, calcd. for
C15H20O3N: 262.1438.
(4-Methoxyphenyl)(4-methylpiperidin-1-yl)methanone
(3p): Yield: 84%; colourless liquid; Rf =0.63 (30% ethyl ace-
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tate in hexane); H NMR (CDCl3, 500 MHz): d=7.38–7.33
(m, 2H), 6.91–6.86 (m, 2H), 3.81 (s, 3H), 3.10–2.50 (m, 2H),
1.90–1.50 (m, 4H), 1.40–1.20 (m, 2H), 0.96 (d, J=6 Hz,
3H); 13C NMR (CDCl3, 125 MHz): d=170.4, 160.7, 129.0,
128.8, 113.8, 55.4, 48.4, 42.7, 34.4, 31.3, 21.9; FT-IR: n=
3458, 2926, 1624, 1177, 839 cmÀ1; HR-MS: m/z=234.1499
[M+H]+, calcd. for C14H20NO2: 234.1494.
(4-Methoxyphenyl)(3-methylpiperidin-1-yl)methanone
(3q): Yield: 78%; colourless liquid; Rf =0.6 (30% ethyl ace-
tate in hexane); 1H NMR (CDCl3, 500 MHz): d=7.34 (d,
J=8.4 Hz, 2H), 6.88 (d, J=8.8 Hz, 2H), 3.90–3.60 (m, 4H),
3.05–2.20 (m, 2H), 1.95–1.35 (m, 4H), 1.35–1.05 (m, 2H),
1.00–0.75 (m, 3H); 13C NMR (CDCl3, 125 MHz): d=170.4,
160.6, 128.9, 128.7, 113.7, 55.4, 48.5, 43.1, 33.3, 31.4, 26.0,
19.0; FT-IR: n=3420, 2929, 1619, 1175, 844 cmÀ1; HR-MS:
m/z=232.1489 [M+H]+, calcd. for C14H20NO2: 234.1494.
(4-Methoxyphenyl)(2-methylpiperidin-1-yl)methanone
(3r): Yield: 65%; colourless liquid; Rf =0.66 (30% ethyl ace-
Ethyl 4-(piperidine-1-carbonyl)benzoate (3k): Yield: 66%;
orange sticky oil; Rf =0.50 (50% ethyl acetate in hexane);
1H NMR (400 MHz, CDCl3): d=8.06–8.0 (m, 2H), 7.44–7.38
(m, 2H), 3.89 (s, 3H), 3.67 (bs, 2H), 3.25 (bs, 2H), 1.64 (s,
4H), 1.47 (m, 2H); 13C NMR (100 MHz, CDCl3): d=169.3,
166.4, 140.8, 130.9, 129.8, 126.8, 52.3, 48.7, 43.1, 25.6, 24.5;
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tate in hexane); H NMR (CDCl3, 500 MHz): d=7.30–7.20
(m, 2H), 6.82 (d, J=10.5 Hz, 2H), 4.60–4.30 (brs, 1H), 4.10–
3.30 (brs, 1H), 3.73 (s, 3H), 2.91 (t, J=16.5 Hz, 1H), 1.70–
1.50 (m, 4H), 1.50–1.30 (m, 2H), 1.20–1.10 (m, 3H);
13C NMR (CDCl3, 125 MHz): d=170.5, 160.4, 129.2, 128.4,
113.7, 55.3, 47.4, 40.4, 30.4, 26.1, 19.0, 16.1; FT-IR: n=3438,
2934, 1620, 1175, 842 cmÀ1; HR-MS: m/z=234.1497 [M+
H]+, calcd. for C14H20NO2: 234.1494.
FT-IR: n=2939, 2851, 1724, 1632, 1506, 1278, 1111 cmÀ1
;
HR-MS: m/z=248.1283 [M+H]+, calcd. for C14H18O3N:
248.1281.
Methyl 3-(piperidine-1-carbonyl)benzoate (3l): Yield:
66%; orange sticky oil; Rf =0.50 (50% ethyl acetate in
hexane); 1H NMR (400 MHz, CDCl3): d=8.06–8.01 (m,
2H), 7.58–7.53 (m, 1H), 7.48–7.42 (m, 1H), 3.89 (s, 3H),
(4-Methoxyphenyl)(morpholino)methanone (3s): Yield:
84%; colourless liquid; Rf =0.15 (30% ethyl acetate in
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