C13H15FO, 206.1101 found 206.1104. Following the procedure
described for 1e, the ketone (3.0 g, 14.5 mmol) was converted
into its oxime (3.1 g, 95% yield), mp 108–10 °C (EtOAc–
petrol). The oxime (3.0 g, 13.5 mmol) was converted into 7
(1.4 g, 47% yield), purified by column chromatography on
silica, eluting with 1% MeOH–Et2O mp 112–4 °C (EtOAc–
eluting with 2% MeOH–Et2O (0.46 g, 83% yield) mp 93–5 °C
(EtOAc–petroleum ether). H-NMR (500 MHz) δ = 1.24–1.33
1
(2H, m), 1.67 (2H, quintet, J = 7.7 Hz), 2.05 (2H, quartet, J =
7.8 Hz), 2.12 (2H, t, J = 7.5 Hz), 2.75 (3H, d, J = 3.7 Hz), 3.88
(1H, t, J = 7.8 Hz), 5.59 (1H, brs), 7.16 (2H, t, J = 7.1 Hz),
7.20–7.30 (8H, m), 13C-NMR + DEPT (125 MHz) δ = 25.8
(CH2), 26.4 (CH3), 27.7 (CH2), 35.4 (CH2), 36.5 (CH2), 51.2
(CH), 126.2 (CH), 127.9 (CH), 128.5 (CH), 145.1 (C), 173.8
(C). LRMS (EI) 281, 167; HRMS calcd for C19H23NO,
281.1774 found 281.1773. FT IR (neat) 2927, 1633, 1572, 1492,
1
petroleum ether). H-NMR (500 MHz) δ = 1.40–1.56 (2H, m),
1.70–2.00 (5H, m), 2.41 (1H, dt, J = 4.5, 12.8 Hz), 2.63 (1H, dt,
J = 3.3, 12.7 Hz), 4.65 (1H, dt, J = 3.6, 11.2 Hz), 5.85 (1H, brd,
J = 9.7 Hz), 7.04 (2H, t, J = 8.6 Hz), 7.30 (2H, dd, J = 5.2, 8.6
Hz). 13C-NMR + DEPT (125 MHz) δ = 24.6 (CH2), 26.1 (CH2),
28.4 (CH2), 33.6 (CH2), 38.6 (CH2), 55.2 (CH), 115.8 (CH, d, J
= 21 Hz), 1281 (CH, d, J = 8 Hz), 137.2 (C, d, J = 3 Hz), 162.1
(C, d, J = 247 Hz), 176.6 (C). LRMS (CI) 222; HRMS calcd for
C13H17FNO, 222.1294 found 222.1294. FT IR (neat) 3198,
2944, 2925, 1648, 1602, 1516, 1453, 1404, 1228, 1151, 837,
1452, 1443, 1156, 760, 747, 706, 693 cm−1
.
Acknowledgements
The authors would like to thank Dr Lisa D. Haigh for the mass
spectra and Dr Abil E. Aliev for assistance with NMR
interpretation.
812, 798, 782, 754 cm−1
.
N-Methyl-3,3-diphenyl-propionamide 12
References
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the extraction solvent which was recrystallised from EtOAc–
petroleum ether (0.45 g, 95% yield) mp 76–7 °C. 1H-NMR
(500 MHz) δ = 2.64 (1.5H, s), 2.65 (1.5H, s), 2.88 (2H, d, J =
7.8 Hz), 4.58 (1H, t, J = 7.8 Hz), 5.25 (1H, brs), 7.17–7.32
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C16H17NO, 239.1305 found 239.1302. FT IR (neat) 3329, 1640,
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6,6-Diphenylhexanoic acid methylamide 14
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This journal is © The Royal Society of Chemistry 2012
Org. Biomol. Chem., 2012, 10, 3244–3252 | 3251