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D. Marosvolgyi-Hasko et al. / Tetrahedron 67 (2011) 1036e1040
1040
131.8,131.7,128.0,124.0,122.8, 59.8, 51.9, 47.2, 29.0,19.4,19.1. IR (KBr,
(cmꢁ1)): 1730 (COO), 1683 (CON); MS (m/z/rel int.): 247(Mþ)/30,
64.01; H, 7.23; N, 7.25. Rf (4% EtOH/CHCl3) 0.40. Pale yellow waxy
material. Yield: 269 mg (72%).
n
204/36,188/100,134/29. Analysis calculated for C14H17NO3 (247.29):
C, 68.00; H, 6.93; N, 5.66. Found: C, 68.17; H, 6.67; N, 5.50. Rf (10%
EtOAc/CHCl3) 0.77. Yellow waxy material. Yield: 185 mg (75%).
4.5.11. 2-Iodobenzylamine (5)28. White crystals, mp 63e65 ꢀC. 13C
NMR (CDCl3)
d: 145.0, 139.3, 128.5 (2C), 128.3, 98.9, 51.3.
4.5.6. 2-(1-Piperidylmethyl)-N,N-(pentan-1,5-diyl)benzamide
4.5.12. 1,2-Bis(1-oxo-1,3-dihydro-isoindol-2-yl)-methanone (6a). 1H
(4f). 1H NMR (CDCl3)
d
: 7.40 (d, 7.8 Hz,1H, AreH); 7.15e7.28 (m, 2H,
NMR (CDCl3) : 7.92 (d, 7.8 Hz, 1H, AreH); 7.65 (t, 7.8 Hz,1H, AreH);
d
AreH); 7.12 (d, 7.8 Hz, 1H, AreH); 3.93e4.00 (m, 1H, NCHaHb);
3.63e3.69 (m, 1H, NCHaHb); 3.35e3.42 (m, 1H, NCHaHb); 3.20 (br s,
2H, AreCH2); 3.02e3.11 (m, 1H, NCHaHb); 2.35 (br s, 4H, N(CH2)2);
7.48e7.55 (m, 2H, AreH); 5.02 (s, 2H, CH2). 13C NMR (CDCl3)
d
:
171.0, 166.4, 141.4, 133.8, 130.9, 128.6, 125.4, 123.2, 49.0. IR (KBr,
n
(cmꢁ1)): 1682 (NC(O)N). MS (m/z/rel int.): 292(Mþ)/60, 160/100,
132/36, 116/35, 104/36, 77/40. Analysis calculated for C17H12N2O3
(292.29): C, 69.86; H, 4.14; N, 9.58. Found: C, 69.70; H, 4.41; N, 9.25.
Rf (10% EtOAc/CHCl3) 0.61. Brown waxy material. Yield: 18 mg (6%).
1.35e1.73 (m,12H, 2ꢂ(CH2)3). 13C NMR (CDCl3)
d: 170.0,137.0,136.5,
129.9, 128.3, 126.7, 125.8, 60.8, 54.7 (double intensity), 48.2, 42.4,
26.3, 26.0 (double intensity), 25.7, 24.6, 24.3. IR (KBr,
n
(cmꢁ1)):
1635 (CON). MS (m/z/rel int.): 286(Mþ)/3. 202/30, 188/11, 172/28,
84/100. Analysis calculated for C18H26N2O (286.42): C, 75.48; H,
9.15; N, 9.78. Found: C, 75.23; H, 9.43; N, 9.55. Rf (6% EtOH/CHCl3)
0.63. Orange waxy material. Yield: 255 mg (89%).
4.5.13. 1,2-Bis(1-oxo-1,3-dihydro-isoindol-2-yl)-ethan-1,2-dione
(6b). MS (m/z/rel int.): 320(Mþ)/10, 292/7, 207/3, 160/100, 116/27,
77/25.
4.5.7. 2-(N-Morpholylmethyl)-iodobenzene (3g). 1H NMR (CDCl3)
d:
Acknowledgements
7.81 (d, 7.8 Hz, 1H, AreH); 7.40 (d, 7.8 Hz, 1H, AreH); 7.31 (t, 7.8 Hz,
1H, AreH); 6.94 (t, 7.8 Hz, 1H, AreH); 3.67e3.73 (m, 4H, O(CH2)2);
3.50 (s, 2H, AreCH2); 2.46e2.52 (m, 4H, N(CH2)2). 13C NMR (CDCl3)
The authors thank the Hungarian Research Fund (CK78553 and
NK77784) for the financial support and Johnson Matthey for the
loan of palladium(II) acetate.
d
: 138.7, 138.1, 128.9, 127.3, 126.5, 99.2, 65.6 (double intensity), 65.3,
52.0 (double intensity). IR (KBr,
n
(cmꢁ1)): 1014 (C-I); MS (m/z/rel
int.): 303(Mþ)/86, 272/10, 217/100, 176/8, 146/62. Analysis calcu-
lated for C11H14NOI (303.14): C, 43.58; H, 4.65; N, 4.62. Found: C,
43.39; H, 4.77; N, 4.40. Rf (40% EtOAc/CHCl3) 0.73. Brown waxy
material. Yield: 167 mg (55%).
Supplementary data
Supplementary data associated with this article can be found in
4.5.8. 2-(N-Morpholylmethyl)-N,N-(30-oxapentan-1,5-diyl)benza-
References and notes
mide (4g). 1H NMR (CDCl3)
d: 7.31 (d, 7.8 Hz, 1H, AreH); 7.18e7.28
(m, 2H, AreH); 7.11 (d, 7.8 Hz, 1H, AreH); 3.48e3.79 (m, 12H,
NCH2þ2ꢂO(CH2)2þAreCH2); 3.10e3.24 (m, 2H, NCH2); 2.35 (m,
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4747e4751.
4H, N(CH2)2). 13C NMR (CDCl3)
d: 168.8, 134.3, 128.9, 127.3, 127.0,
125.8, 124.9, 65.5 (double intensity), 65.3, 65.2, 59.1, 52.0 (double
n
(cmꢁ1)): 1635 (CON); MS (m/z/rel
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intensity), 46.0, 40.5. IR (KBr,
int.): 290(Mþ)/5, 204/80, 203/90, 190/35, 174/70, 145/61, 119/82, 86/
100. Analysis calculated for C16H22N2O3 (290.36): C, 66.18; H, 7.64;
N, 9.65. Found: C, 66.01; H, 7.86; N, 9.44. Rf (6% EtOH/CHCl3) 0.55.
Dark brown waxy material. Yield: 209 mg (72%).
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7. Delacroix, T.; Berillon, L.; Cahiez, G.; Knochel, P. J. Org. Chem. 2000, 65,
8108e8110.
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Weinheim, 1998; Vol. IeII.
4.5.9. 2-(20-(Methoxycarbonyl)pyrrolidin-1-yl-methyl)-iodobenzene
(3h). 1H NMR (CDCl3)
d: 7.80 (d, 7.8 Hz, 1H, AreH); 7.47 (d, 7.8 Hz,
1H, AreH); 7.31 (t, 7.8 Hz,1H, AreH); 6.92 (t, 7.8 Hz,1H, AreH); 3.92
(d, 13.9 Hz, 1H, AreCHaHb); 3.72 (d, 13.9 Hz, 1H, AreCHaHb); 3.63 (s,
3H, OCH3); 3.40e3.46 (m, 1H, CHCOO); 3.01e3.08 (m, 1H, NCHaHb);
2.48e2.55 (m, 1H, NCHaHb); 1.75e2.20 (m, 4H, (CH2)2). 13C NMR
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actions: In Modern Carbonylation Methods; Kollar, L., Ed.; Wiley-VCH: Wein-
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(CDCl3)
51.6, 50.2, 27.9, 21.9. IR (KBr,
d: 173.0, 139.6, 137.8, 128.9, 127.2, 126.6, 98.5, 63.8, 60.8,
n
(cmꢁ1)): 1733 (COO), 1639 (CON). MS
(m/z/rel int.): 345(Mþ)/2, 286/100, 217/59, 158/3, 90/12. Analysis
calculated for C13H16NO2I (345.18): C, 45.24; H, 4.67; N, 4.06. Found:
C, 45.03; H, 4.43; N, 3.86. Rf (20% EtOAc/CHCl3) 0.76. Dark brown
waxy material. Yield: 172 mg (50%).
4.5.10. 2-(20-(Methoxycarbonyl)pyrrolidin-1-yl-methyl)-N,N-(10-
(methoxycarbonyl)-butan-1,4-diyl)benzamide (4h). 1H NMR (CDCl3)
22. Amatore, C.; Carre, E.; Jutand, A.; M’Barki, M. A.; Meyer, G. Organometallics
1995, 14, 5605e5614.
d: 7.45 (d, 7.8 Hz, 1H, AreH); 7.18e7.30 (m, 2H, AreH); 7.12 (d,
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€
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M. K. Pure Appl. Chem. 1991, 63, 687e696.
7.8 Hz, 1H, AreH); 3.75 (s, 3H, OCH3); 3.70 (s, 3H, OCH3); 3.20e3.70
(m, 8H, AreCH2þ2ꢂCHCOOþ2ꢂNCH2); 1.75e2.40 (m, 8H, 2x
(CH2)2). 13C NMR (CDCl3)
d: 174.2, 172.8, 169.6, 137.0, 132.1, 128.8,
25. Barnard, C. F. J. Organometallics 2008, 27, 5402e5422.
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26. Takacs, A.; Petz, A.; Kollar, L. Tetrahedron 2010, 66, 4479e4483.
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57, 9697e9710.
128.5, 127.0, 126.1, 65.4, 58.5, 58.2, 55.5, 52.2, 49.1, 47.7, 29.6, 29.1,
24.9, 24.7. IR (KBr,
n
(cmꢁ1)): 1743 (COO), 1636 (CON). MS (m/z/rel
int.): 374(Mþ)/3, 315/80, 245/100, 215/27, 166/48. Analysis calcu-
lated for C20H26N2O5 (374.44): C, 64.16; H, 7.00; N, 7.48. Found: C,
ꢀ
€
28. Erdelyi, M.; Varedian, M.; Skold, C.; Niklasson, I. B.; Nurbo, J.; Persson, A.;
Bergquist, J.; Gogoll, A. Org. Biomol. Chem. 2008, 6, 4356e4373.