530
V. Z. Shirinian et al.
PRACTICAL SYNTHETIC PROCEDURES
(s, 3 H, CH3), 6.69 (d, J = 8.8 Hz, 2 H, ArH), 6.96 (d, J = 8.8 Hz, 2
H, ArH), 7.72–7.82 (m, 4 H, ArH).
(s, 3 H, CH3), 3.85 (s, 3 H, CH3), 6.47–6.56 (m, 2 H, ArH), 6.62 (d,
J = 9.0 Hz, 2 H, ArH), 7.27 (d, J = 9.0 Hz, 1 H, ArH), 7.72 (d,
J = 9.0 Hz, 2 H, ArH).
MS (EI, 70 eV): m/z (%) = 309 (67) [M]+, 294 (58) [M – Me]+, 278
(39) [M – OMe]+, 202 (100).
MS (EI, 70 eV): m/z (%) = 339 (66) [M]+, 324 (100) [M – Me]+, 308
(68) [M – OMe]+.
Anal. Calcd for C20H23NO2: C, 77.64; H, 7.49; N, 4.53. Found: C,
77.33; H, 7.51; N, 4.65.
Anal. Calcd for C21H25NO3: C, 74.31; H, 7.42; N, 4.13. Found: C,
74.24; H, 7.39; N, 4.51.
(2,4-Dimethoxyphenyl)(4-morpholinophenyl)methanone (2d)
White powder; yield: 1.5 g (93%); mp 86–87 °C (PE).
Naphthalen-1-yl[4-(piperidin-1-yl)phenyl]methanone (2i)
Yellowish powder; yield: 1.3 g (83%); mp 78–79 °C (PE).
1H NMR (300 MHz, CDCl3): d = 3.29 (t, J = 5.1 Hz, 4 H, 2 × CH2),
3.68 (s, 3 H, CH3), 3.73 (t, J = 5.1 Hz, 4 H, 2 × CH2), 3.84 (s, 3 H,
CH3), 6.62 (dd, J = 2.2, 8.1 Hz, 1 H, ArH), 6.67 (d, J = 2.2 Hz, 1 H,
ArH), 6.95 (d, J = 8.8 Hz, 2 H, ArH), 7.19 (d, J = 8.1 Hz, 1 H,
ArH), 7.57 (d, J = 8.8 Hz, 2 H, ArH).
1H NMR (300 MHz, CDCl3): d = 1.64–1.73 (m, 6 H, 3 × CH2),
3.35–3.43 (m, 4 H, 2 × CH2), 6.83 (d, J = 9.2 Hz, 2 H, ArH), 7.44–
7.56 (m, 4 H, ArH), 7.78 (d, J = 9.2 Hz, 2 H, ArH), 7.88–8.03 (m,
3 H, ArH).
MS (EI, 70 eV): m/z (%) = 327 (100) [M]+, 312 (78) [M – Me]+, 296
MS (EI, 70 eV): m/z (%) = 315 (100) [M]+.
(44) [M – OMe]+.
Anal. Calcd for C22H21NO: C, 83.78; H, 6.71; N, 4.44. Found: C,
83.86; H, 6.68; N, 4.26.
Anal. Calcd for C19H21NO4: C, 69.71; H, 6.47; N, 4.28. Found: C,
69.81; H, 6.45; N, 4.44.
(4-Hydroxy-2-isopropoxyphenyl)[4-(piperidin-1-yl)phe-
nyl]methanone (2j)
Yellow powder; yield: 1.6 g (96%); mp 103.5–104.5 °C (PE).
(2,4-Dimethoxyphenyl)(2-morpholinophenyl)methanone (2e)
Yellow powder; yield: 1.3 g (81%); mp 82–83 °C (PE).
1H NMR (300 MHz, CDCl3): d = 2.87 (t, J = 4.6 Hz, 4 H, 2 × CH2),
3.34 (t, J = 4.6 Hz, 4 H, 2 × CH2), 3.60 (s, 3 H, CH3), 3.86 (s, 3 H,
CH3), 6.42 (d, J = 2.0 Hz, 1 H, ArH), 6.50 (dd, J = 2.2, 8.5 Hz, 1 H,
ArH), 6.96 (d, J = 7.9 Hz, 1 H, ArH), 7.07 (t, J = 7.2 Hz, 1 H, ArH),
7.35–7.47 (m, 2 H, ArH), 7.55 (d, J = 8.5 Hz, 2 H, ArH).
1H NMR (300 MHz, CDCl3): d = 1.38 (d, J = 6.2 Hz, 6 H, 2 × CH3),
1.64–1.76 (m, 6 H, 3 × CH2), 3.37 (t, J = 5.1 Hz, 4 H, 2 × CH2), 4.63
(sept, J = 6.2 Hz, 1 H, CH), 6.38 (dd, J = 2.2, 8.8 Hz, 1 H, ArH),
6.49 (d, J = 2.2 Hz, 1 H, ArH), 6.91 (d, J = 8.8 Hz, 2 H, ArH), 7.57–
7.68 (m, 3 H, ArH), 12.51 (br s, 1 H, OH).
MS (EI, 70 eV): m/z (%) = 327 (100) [M]+, 312 (63) [M – Me]+, 296
MS (EI, 70 eV): m/z (%) = 339 (69) [M]+, 296 (20) [M – iPr]+, 161
(100).
(56) [M – OMe]+.
Anal. Calcd for C19H21NO4: C, 69.71; H, 6.47; N, 4.28. Found: C,
69.99; H, 6.37; N, 3.96.
Anal. Calcd for C21H25NO3: C, 74.31; H, 7.42; N, 4.13. Found: C,
74.22; H, 7.48; N, 4.07.
(2,4-Dimethoxyphenyl)[4-(piperidin-1-yl)phenyl]methanone
(2f)
(4-Morpholinophenyl)(thien-2-yl)methanone (2k)
Yellow powder; yield: 1.2 g (90%); mp 122–123 °C (PE).
White powder; yield: 1.6 g (98%); mp 112–113 °C (PE).
1H NMR (300 MHz, CDCl3): d = 3.32 (t, J = 5.0 Hz, 4 H, 2 × CH2),
3.87 (t, J = 5.0 Hz, 4 H, 2 × CH2), 6.92 (d, J = 9.1 Hz, 2 H, ArH),
7.15 (dd, J = 3.9, 5.3 Hz, 1 H, ArH), 7.63–7.68 (m, 2 H, ArH), 7.89
(d, J = 9.1 Hz, 2 H, ArH).
1H NMR (300 MHz, CDCl3): d = 1.60–1.75 (m, 6 H, 3 × CH2),
3.30–3.42 (m, 4 H, 2 × CH2), 3.74 (s, 3 H, CH3), 3.86 (s, 3 H, CH3),
6.50–6.56 (m, 2 H, ArH), 6.82 (d, J = 8.5 Hz, 2 H, ArH), 7.30 (d,
J = 9.2 Hz, 1 H, ArH), 7.73 (d, J = 8.5 Hz, 2 H, ArH).
MS (EI, 70 eV): m/z (%) = 273 (100) [M]+.
MS (EI, 70 eV): m/z (%) = 325 (100) [M]+, 310 (54) [M – Me]+, 294
Anal. Calcd for C15H15NO2S: C, 65.91; H, 5.53; N, 5.12. Found: C,
66.03; H, 5.57; N, 5.33.
(47) [M – OMe]+.
Anal. Calcd for C20H23NO3: C, 73.82; H, 7.12; N, 4.30. Found: C,
74.09; H, 7.24; N, 4.47.
[4-(Azepan-1-yl)phenyl][4-(2,3-dihydroindol-1-yl)phe-
nyl]methanone (2l)
(2,4-Dimethoxyphenyl)[4-(pyrrolidin-1-yl)phenyl]methanone
(2g)
Yellowish powder; yield: 1.5 g (95%); mp 129–130 °C (PE).
1H NMR (300 MHz, CDCl3): d = 1.95–2.09 (m, 4 H, 2 × CH2),
3.28–3.42 (m, 4 H, 2 × CH2), 3.74 (s, 3 H, CH3), 3.86 (s, 3 H, CH3),
6.44–6.57 (m, 4 H, ArH), 7.28 (d, J = 7.9 Hz, 1 H, ArH), 7.74 (d,
J = 8.5 Hz, 2 H, ArH).
Yellow powder; yield: 1.6 g (80%); mp 133–134 °C (PE).
1H NMR (300 MHz, CDCl3): d = 1.53–1.61 (m, 4 H, 2 × CH2),
1.77–1.89 (m, 4 H, 2 × CH2), 3.18 (t, J = 8.3 Hz, 2 H, CH2), 3.55 (t,
J = 5.9 Hz, 4 H, 2 × CH2), 4.04 (t, J = 8.3 Hz, 2 H, CH2), 6.71 (d,
J = 8.8 Hz, 2 H, ArH), 6.84 (t, J = 7.3 Hz, 1 H, ArH), 7.14 (d,
J = 7.8 Hz, 1 H, ArH), 7.19–7.29 (m, 3 H, ArH), 7.32 (d, J = 7.8
Hz, 1 H, ArH), 7.77–7.87 (m, 4 H, ArH).
MS (EI, 70 eV): m/z (%) = 311 (60) [M]+, 296 (100) [M – Me]+, 174
MS (EI, 70 eV): m/z (%) = 396 (100) [M]+.
(57).
Anal. Calcd for C27H28N2O: C, 81.78; H, 7.12; N, 7.06. Found: C,
81.91; H, 7.06; N, 7.23.
Anal. Calcd for C19H21NO3: C, 73.29; H, 6.80; N, 4.50. Found: C,
73.41; H, 6.73; N, 4.30.
Acknowledgment
[4-(Azepan-1-yl)phenyl](2,4-dimethoxyphenyl)methanone (2h)
Yellowish powder; yield: 1.7 g (99%); mp 98–99 °C (PE).
1H NMR (300 MHz, CDCl3): d = 1.47–1.63 (m, 4 H, 2 × CH2),
1.69–1.88 (m, 4 H, 2 × CH2), 3.51 (t, J = 6.2 Hz, 4 H, 2 × CH2), 3.74
This work was financially supported by the Russian Foundation for
Basic Research (RFBR Grant – 11-03-00799) and the Russian Aca-
demy of Sciences (Program No. 22).
Synthesis 2012, 44, 527–531
© Thieme Stuttgart · New York