反应详情

To a solution of 8-phenyl octanoic acid (28.6 g, 129.8 mmol, 1 eq) in CH2Cl2 (100 mL) cooled to 0° C. was added oxalyl chloride (17 mL, 195 mmol, 1.5 eq) dropwise via an addition funnel over 30 minutes. Upon the completion of the addition, the ice bath was removed and the reaction was stirred at rt for 2 h. It was then heated at reflux for 30 minutes. The reaction was cooled to rt and concentrated in vacuo to afford a yellow oil. It was added as a solution in Et2O (100 mL) to a solution of condensed methyl amine (˜20 mL) in Et2O (200 mL) at −78° C. Immediately, a white precipitate formed. The cold bath was removed and the reaction was allowed to stir overnight warming to rt under a stream of N2. The residue was washed with Et2O and concentrated to afford N-methyl-8-phenyloctanamide (25.2 g, 83%) as a yellow-white solid. 1H NMR (CDCl3) δ 7.68–7.10 (m, 5H); 5.42 (bs, 1H); 3.80 (m, 3H); 2.60 (m, 2H); 2.18 (m, 2H); 1.60 (m, 4H); 1.30 (m, 8H).

1. additionUpon the completion of the addition
2. customthe ice bath was removed
3. temperatureIt was then heated
4. temperatureat reflux for 30 minutes
5. temperatureThe reaction was cooled to rt
6. concentrationconcentrated in vacuo
7. customto afford a yellow oil
8. customImmediately, a white precipitate formed
9. customThe cold bath was removed
10. stirringto stir overnight
11. temperaturewarming to rt under a stream of N2
12. washThe residue was washed with Et2O
13. concentrationconcentrated