反应详情

To a solution of N-methyl-8-phenyloctanamide (25.2 g, 108.0 mmol, 1 eq) in THF (500 mL) cooled to 0° C. was added lithium aluminum hydride (12.3 g, 466.8 mmol, 4.3 eq) portionwise over 20 minutes. The cold bath was removed and the reaction was stirred at rt 3 hours. The reaction was then heated at reflux for 2½ hours. It was then cooled to rt and quenched by the slow addition of H2O (30 mL). EtOAc (300 mL) was added, followed by 2 M NaOH (40 mL). The solids were then filtered off and washed with EtOAc. The filtrate was dried over MgSO4 and concentrated in vacuo to afford N-methyl-N-(8-phenyloctyl)amine (19.7 g, 83%) as a light yellow oil. 1H NMR (CDCl3) δ 7.30–7.14 (m, 5H); 2.63–2.52 (m, 4H); 2.43 (s, 3H); 2.05 (s, 1H); 1.62 (m, 4H); 1.30 (m, 8H).

1. customThe cold bath was removed
2. temperatureThe reaction was then heated
3. temperatureat reflux for 2½ hours
4. temperatureIt was then cooled to rt
5. customquenched by the slow addition of H2O (30 mL)
6. additionEtOAc (300 mL) was added
7. filtrationThe solids were then filtered off
8. washwashed with EtOAc
9. dry with materialThe filtrate was dried over MgSO4
10. concentrationconcentrated in vacuo