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15. General procedure:
Synthesis of 1-morpholino-2-phenyl ethanone
In a round bottomed flask 0.01 mol (1.36 g) phenyl acetic acid and 0.012 mol
(1.94 g) of CDI were added. The reaction mixture was mixed and grinded with a
spatula. CO2 gas starts releasing with increase in temperature and solid
reaction mixture was turned to pale yellow liquid within 5 min.
0.001 mol (0.1 g) Imidazole. hydrochloride, 0.01 mol (0.87 g) of morpholine,
and 1 mL of water were added to it. The reaction mixture was kept at room
temperature for another 10 min. Dilute hydrochloride solution was added to it
and the aqueous layer was washed with ethyl acetate. The organic layer was
dried over anhydrous Na2SO4 and concentrated to give pure product.
7. (a) Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006,
4, 2337; (b) Dale, D. J.; Dunn, P. J.; Golighty, C.; Hughes, M. L.; Levett, P. C.;
Pearce, A. K.; Searle, P. M.; Ward, G.; Wood, A. S. Org. Process Res. Dev. 2000, 4,
17.
All the compounds of Table 3 are known compounds.6–11,14
1H NMR and
C NMR of some representative compounds of Table 3.
13
1-morpholino-2-phenylethanone 1H NMR (400 MHz, CDCl3) d 7.32–7.26 (m, 2H),
7.25–7.22(m, 3H), 3.70 (s, 2H), 3.61 (br s, 4H), 3.43 (dt, J = 9.1, 3.9 Hz, 4H). 13
C
8. Dunn, P. J.; Hoffmann, W.; Kang, Y.; Mitchell, J. C.; Snowden, M. J. Org. Process.
Res. Dev. 2005, 9, 956.
9. (a) Rannard, S. P.; Davis, N. J. Org. Lett. 2010, 14, 2117; (b) Rannard, S. P.; Davis,
N. J. Org. Lett. 2010, 12, 4232.
10. (a) Dunn, P. J.; Hughes, M. L.; Searle, P. M.; Wood, A. S. Org. Process Res. Dev.
2003, 7, 244; (b) Bright, R.; Dale, D. J.; Dunn, P. J.; Hussain, F.; Kang, Y.; Mason,
C.; Mitchell, J. C.; Snowden, M. J. Org. Process Res. Dev. 2004, 8, 1054; (c)
Aboussafy, C. L.; Jones, B. P.; Price, K. E.; Hardink, M. A.; McLaughlin, R. W.;
Lillie, B. M.; Hawkins, J. M.; Vaidyanathan, R. Org. Lett. 2010, 2, 324.
11. (a) Woodman, E. K.; Chaffey, J. G. K.; Hopes, P. A.; Hose, D. R. J.; Gilday, J. P. Org.
Process Res. Dev. 2009, 13, 106; (b) Vaidyanathan, R.; Kalthod, V. G.; Ngo, D. P.;
Manley, J. M.; Lapekas, S. P. J. Org. Chem. 2004, 69, 2565.
NMR (100 MHz, CDCl3) d 169.6, 134.8, 128.8, 128.5, 126.9, 66.7, 66.4, 46.5, 42.1,
40.8.
N-(4-Nitrobenzoyl)morpholine: 1H NMR(400 MHz, CDCl3): d 8.29 (d, J = 6.9 Hz,
2H), 7.59 (d, J = 6.9 Hz, 2H), 3.25–3.98 (m, 8H).13C NMR(100 MHz, CDCl3): d
168.3, 148.7, , 141.7, 128.4, 124.2, 67.0, 48.5, 42.9.
N-Benzoylmorpholine: 1H NMR(400 MHz, CDCl3): d 7.41–7.36 (s, 5H), 3.81–3.67
(br m, 4H), 3.65–3.51 (br m, 2H), 3.51–3.35 (br m, 2H); 13C NMR (100 MHz,
CDCl3): 170.6, 135.5, 130.2, 128.9, 127.4, 67.0, 48.4, 42.7.
N-Benzoylpiperidine: 1H NMR(400 MHz, CDCl3): d 7.37 (s, 5H), 3.69 (br s, 2H),
3.31 (br s, 2H), 1.65 (br s, 4H), 1.48 (br s, 2H) ; 13C NMR (100 MHz, CDCl3):
170.5, 136.8, 129.5, 128.6, 127.0, 48.9, 43.2, 26.8, 25.8, 24.8.
N-(tert-Butoxycarbonyl)-morpholine: 1H NMR (400 MHz, CDCl3): d 1.46 (s, 9H),
3.41 (t, J = 4.8 Hz, 4H), 3.64 (t, J = 4.6 Hz, 4H); 13C NMR (100 MHz, CDCl3):
d = 28.4 (CH3), 44.2 (CH2), 66.6 (CH2), 79.9 (C), 154.7 (C@O).
12. CDCl3, DMSO, C6D6, THF and neat. In neat condition reaction was performed
without solvent and NMR was recorded in CDCl3.