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Organic & Biomolecular Chemistry
(d, J = 7.20 Hz, 2H), 7.47 (t, J = 7.20 Hz, 1H), 7.37 (t, J = 7.20 8.10 Hz, 2H), 7.16 (d, J = 8.10 Hz, 2H), 4.06 (q, J = 6.90 Hz, 1H),
Hz, 2H), 4.09 (q, J = 6.60 Hz, 1H), 2.80 (m, 4H), 2.52 (m, 4H), 2.49 (m, 4H), 2.32 (s, 3H), 1.49 (m, 4H), 1.34 (m, 2H), 1.20 (d,
1.19 (d, J = 6.60 Hz, 3H).
J = 6.90 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 200.48, 143.75,
Phenyl-2-thiomorpholinobutan-1-one (10a). Yellow liquid, 133.88, 129.08, 129.05, 64.82, 50.80, 26.16, 24.35, 21.72, 11.84,
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89% yield (111 mg). H NMR (300 MHz, CDCl3) δ 7.98 (d, J = 11.79. HRMS (APCI) Calcd for C15H21NO [M + H]+ 232.1696,
7.23 Hz, 2H), 7.54 (t, J = 7.25 Hz, 1H), 7.43 (t, J = 7.24 Hz, 2H), found 232.1696.
3.93 (m, 1H), 2.88 (m, 4H), 2.56 (m, 4H), 1.87 (m, 1H), 1.69 (m,
1-(4-Methoxyphenyl)-2-(piperidin-1-yl)
propan-1-one
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1H), 0.86 (t, J = 7.35 Hz, 3H). 13C NMR (125 MHz, CDCl3) (18a). Yellow liquid, 92% yield (114 mg). H NMR (300 MHz,
δ 199.62, 137.66, 133.23, 128.82, 128.77, 70.94, 52.28, 28.85, CDCl3) δ 8.12 (d, J = 8.70 Hz, 2H), 6.90 (d, J = 8.70 Hz, 2H),
18.91, 11.64. HRMS (APCI) Calcd for C14H19NOS [M + H]+ 4.00 (q, J = 6.90 Hz, 1H), 3.85 (s, 3H), 2.52 (m, 4H), 1.51 (m,
250.1260, found 250.1261.
4H), 1.41 (m, 2H), 1.24 (d, J = 6.90 Hz, 3H). 13C NMR
2-Thiomorpholino-1-p-tolylpropan-1-one
liquid, 82% yield (102 mg). H NMR (300 MHz, CDCl3) δ 7.87 65.50, 55.76, 51.18, 26.67, 24.78, 11.94. HRMS (APCI) Calcd for
(d, J = 8.10 Hz, 2H), 7.15 (d, J = 8.10 Hz, 2H), 4.03 (m, 1H), 2.77 C15H21NO2 [M + H]+ 248.1645, found 248.1647.
(11a). Yellow (125 MHz, CDCl3) δ 199.98, 163.59, 131.62, 129.82, 113.74,
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(m, 4H), 2.50 (m, 4H), 2.32 (s, 3H), 1.15 (d, J = 6.90 Hz, 3H).
1-(4-Chlorophenyl)-2-(piperidin-1-yl)
propan-1-one
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13C NMR (125 MHz, CDCl3) δ 199.45, 143.45, 133.45, 128.80, (19a). Yellow liquid, 97% yield (122 mg). H NMR (300 MHz,
128.78, 64.76, 51.37, 28.17, 21.45, 9.89. HRMS (APCI) Calcd for CDCl3) δ 8.08 (d, J = 8.40 Hz, 2H), 7.39 (d, J = 8.40 Hz, 2H),
C14H19NOS [M + H]+ 250.1260, found 250.1256.
4.01 (q, J = 6.90 Hz, 1H), 2.51 (m, 4H), 1.51 (m, 4H), 1.39 (m,
1-(4-Methoxyphenyl)-2-thiomorpholinopropan-1-one (12a). 2H), 1.23 (d, J = 6.90 Hz, 3H). 13C NMR (125 MHz, CDCl3)
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Yellow liquid, 80% yield (106 mg). H NMR (300 MHz, CDCl3) δ 200.04, 139.42, 134.98, 130.88, 128.86, 65.85, 50.95, 26.58,
δ 8.03 (d, J = 9.00 Hz, 2H), 6.89 (d, J = 9.00 Hz, 2H), 4.05 (q, J = 24.63, 10.82. HRMS (APCI) Calcd for C14H18ClNO [M + H]+
6.60 Hz, 1H), 3.84 (s, 3H), 2.83 (m, 4H), 2.57 (m, 4H), 1.21 (d, 252.1150, found 252.1150.
J = 6.60 Hz, 3H). 13C NMR (125 MHz, CDCl3) δ 198.80, 163.54,
Methyl 2-phenyl-2-(piperidin-1-yl) acetate (20a).20 Yellow
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131.51, 129.35, 113.67, 65.23, 55.67, 51.83, 28.63, 10.39. HRMS liquid, 87% yield (101 mg). H NMR (300 MHz, CDCl3) δ 7.36
(APCI) Calcd for C14H19NO2S [M + H]+ 266.1209, found (m, 2H), 7.23 (m, 3H), 3.90 (s, 1H), 3.59 (s, 3H), 2.29 (m, 4H),
266.1213.
1.51 (m, 4H), 1.35 (m, 2H).
1-(4-Chlorophenyl)-2-thiomorpholinopropan-1-one (13a).
Ethyl 2-(piperidin-1-yl)-2-phenylacetate (21a). Yellow liquid,
Yellow liquid, 74% yield (99 mg). H NMR (300 MHz, CDCl3) 84% yield (104 mg). 1H NMR (300 MHz, CDCl3) δ 7.36 (m, 2H),
δ 7.99 (d, J = 8.40 Hz, 2H), 7.39 (d, J = 8.40 Hz, 2H), 4.05 (q, J = 7.23 (m, 3H), 4.06 (m, 2H), 3.87 (s, 1H), 2.31 (m, 4H), 1.50 (m,
6.90 Hz, 1H), 2.81 (m, 4H), 2.58 (m, 4H), 1.22 (d, J = 6.90 Hz, 4H), 1.35 (m, 2H), 1.11 (t, J = 7.20 Hz, 3H). 13C NMR (125 MHz,
3H). 13C NMR (125 MHz, CDCl3) δ 199.15, 139.58, 134.72, CDCl3) δ 172.06, 136.65, 129.08, 128.65, 128.34, 75.23, 60.94,
130.81, 128.94, 65.78, 51.83, 28.68, 9.77. HRMS (APCI) Calcd 52.62, 26.06, 24.64, 14.39. HRMS (APCI) Calcd for C15H21NO2
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for C13H16ClNOS [M + H]+ 270.0714, found 270.0712.
[M + H]+ 248.1645, found 248.1643.
2-Thiomorpholino-1-(thiophen-2-yl)butan-1-one (14a). Yellow
2-(Piperidin-1-yl)-1-(thiophen-2-yl)butan-1-one (22a). Yellow
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liquid, 84% yield (107 mg). H NMR (500 MHz, CDCl3) δ 7.83 liquid, 93% yield (110 mg). H NMR (500 MHz, CDCl3) δ 7.90
(d, J = 4.00 Hz, 1H), 7.58 (d, J = 4.00 Hz, 1H), 7.08 (t, J = 4.00 (d, J = 4.00 Hz, 1H), 7.56 (d, J = 4.00 Hz, 1H), 7.09 (t, J = 4.00 Hz,
Hz, 1H), 3.61 (m, 1H), 2.89 (m, 4H), 2.62 (m, 4H), 1.83 (m, 1H), 1H), 3.53 (m, 1H), 2.59 (m, 2H), 2.50 (m, 2H), 1.82 (m, 1H), 1.74
1.69 (m, 1H), 0.88 (t, J = 5.00 Hz, 3H). 13C NMR (125 MHz, (m, 1H), 1.55 (m, 4H), 1.39 (m, 2H), 0.86 (t, J = 7.50 Hz, 3H).
CDCl3) δ 192.09, 142.19, 133.01, 132.08, 126.93, 72.67, 51.51, 13C NMR (125 MHz, CDCl3) δ 194.49, 143.32, 133.97, 133.08,
27.54, 18.45, 10.77. HRMS (APCI) Calcd for C12H17NOS2 127.82, 73.85, 51.66, 26.52, 24.79, 20.54, 11.71. HRMS (APCI)
[M + H]+ 256.0824, found 256.0823.
Calcd for C13H19NOS [M + H]+ 238.1260, found 238.1257.
1-Phenyl-2-(piperidin-1-yl)propan-1-one
(15a).9 Yellow
2-(3,4-Dihydroisoquinolin-2(1H)-yl)-1-phenylpropan-1-one
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liquid, 95% yield (103 mg). H NMR (300 MHz, CDCl3) δ 8.09 (23a).9 Yellow liquid, 94% yield (125 mg). H NMR (300 MHz,
(m, 2H), 7.51(m, 1H), 7.43 (m, 2H), 4.13 (q, J = 6.90 Hz, 1H), CDCl3) δ 8.06 (m, 2H), 7.46 (m, 1H), 7.35 (m, 2H), 6.99 (m,
2.56 (m, 4H), 1.54 (m, 4H), 1.40 (m, 2H), 1.26 (d, J = 6.90 Hz, 4H), 4.24 (q, J = 6.90 Hz, 1H), 3.81 (d, J = 15.0 Hz, 1H), 3.76 (d,
3H).
1-Phenyl-2-(piperidin-1-yl)butan-1-one (16a). Yellow liquid,
J = 15.0 Hz, 1H), 2.77 (m, 4H), 1.31 (d, J = 6.90 Hz, 3H).
2-(3,4-Dihydroisoquinolin-2(1H)-yl)-1-phenylbutan-1-one
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95% yield (110 mg). H NMR (500 MHz, CDCl3) δ 8.05 (d, J = (24a). Yellow liquid, 95% yield (133 mg). H NMR (300 MHz,
7.00 Hz, 2H), 7.50(d, J = 7.00 Hz, 1H), 7.42 (m, J = 7.00 Hz, 2H), CDCl3) δ 8.00 (m, 2H), 7.43 (m, 1H), 7.33 (m, 2H), 6.96 (m,
3.89 (q, J = 7.50 Hz, 1H), 2.57 (m, 2H), 2.49 (m, 2H), 1.87 (m, 4H), 4.06 (q, J = 4.80 Hz, 1H), 3.80 (d, J = 15.0 Hz, 1H), 3.72 (d,
1H), 1.70 (m, 1H), 1.49 (m, 4H), 1.36 (m, 2H), 0.83 (t, J = 7.50 J = 15.0 Hz, 1H), 2.80 (m, 2H), 2.72 (m, 2H), 1.92 (m, 1H), 1.75
Hz, 3H). 13C NMR (125 MHz, CDCl3) δ 200.41, 137.87, 132.78, (m, 1H), 0.82 (d, J = 7.20 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ
128.61, 128.43, 70.58, 51.03, 26.52, 24.57, 19.49, 11.29. HRMS 200.59, 137.84, 135.45, 135.00, 133.45, 129.19, 129.07, 128.99,
(APCI) Calcd for C15H21NO [M + H]+ 232.1696, found 232.1696. 126.97, 126.44, 125.97, 70.12, 52.76, 47.70, 30.27, 19.89, 11.68.
2-(Piperidin-1-yl)-1-p-tolylpropan-1-one (17a). Yellow liquid, HRMS (APCI) Calcd for C19H21NO [M + H]+ 280.1696, found
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94% yield (109 mg). H NMR (300 MHz, CDCl3) δ 7.93 (d, J = 280.1695.
5514 | Org. Biomol. Chem., 2014, 12, 5509–5516
This journal is © The Royal Society of Chemistry 2014