反応 #10262

反応方程式

(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(2-propanon-1-yl)piperazine

O-[2-(dimethylamino)ethyl]hydroxylamine dihydrochloride

sodium acetate

→

1-{(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-piperazin-4-yl}-2-propanone O-[2-(dimethylamino)-ethyl]oxime

収率 104.0%

溶媒

methanol

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度under reflux for 2 h
3. 3
   その他The solvent was removed in vacuo
4. 4
   workup.ADDITIONthe residue was treated with dichloromethane and NAOH (aq, 2N)
5. 5
   その他The layers were separated
6. 6
   その他the organic layer was dried
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH4OH 92/7.5/0.5)

実験手順

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(2-propanon-1-yl)piperazine (255 mg), O-[2-(dimethylamino)ethyl]hydroxylamine dihydrochloride (89 mg), sodium acetate (catalytically), and methanol (10 mL) was heated under reflux for 2 h. The solvent was removed in vacuo, and the residue was treated with dichloromethane and NAOH (aq, 2N). The layers were separated, the organic layer was dried and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH4OH 92/7.5/0.5) to afford 1-{(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-piperazin-4-yl}-2-propanone O-[2-(dimethylamino)-ethyl]oxime 0.31 g (>95%) as an E/Z mixture. Rf 0.26 (CH2Cl2/MeOH/NH4OH 92/7.5/0.5).

出典