反応 #6997

反応方程式

2-(3,4-dichlorophenoxy)-5-fluoro-N-methyl benzamide

→

[2-(3,4-DICHLOROPHENOXY)-5-FLUOROBENZYL]-METHYLAMINE

溶媒

tetrahydrofuran

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas treated via syringe with 4.0 mL (4.0 mmol) of 1.0 M
2. 2
   温度and the mixture was heated
3. 3
   温度to reflux for a total of 48 hr
4. 4
   その他The reaction was quenched by the addition of 25 mL of 6N HCl
5. 5
   温度heating
6. 6
   温度to reflux until the free amine
7. 7
   workup.ADDITIONThe cooled mixture was then diluted with water
8. 8
   抽出extracted with EtOAc
9. 9
   洗浄The combined organic layers were washed with water and saturated NaCl
10. 10
    乾燥dried with MgSO4
11. 11
    ろ過filtered
12. 12
    濃縮concentrated in vacuo to the free base as a light brown oil, 0.164 g, 54%)

実験手順

Under N2, a mixture of 0.313g (1.0 mmol) of 2-(3,4-dichlorophenoxy)-5-fluoro-N-methyl benzamide in 5.0 mL of anhydrous tetrahydrofuran (THF) was treated via syringe with 4.0 mL (4.0 mmol) of 1.0 M BH3 in THF (Aldrich Chem. Co.). and the mixture was heated to reflux for a total of 48 hr. The reaction was quenched by the addition of 25 mL of 6N HCl and heating to reflux until the free amine could be detected by tic (CHCl3:CH3OH:TEA, (95:5:1)). The cooled mixture was then diluted with water, basified with K2CO3and extracted with EtOAc. The combined organic layers were washed with water and saturated NaCl, then dried with MgSO4, filtered and concentrated in vacuo to the free base as a light brown oil, 0.164 g, 54%). This compound was converted to the hydrochloride salt as described previously, m.p. 200–202°.

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