反応 #657287

反応方程式

1-methoxy-4-methylamino-piperidine-4-carboxylic acid

methanol

thionyl chloride

→

1-methoxy-4-methylamino-piperidine-4-carboxylic acid methyl ester

反応条件

後処理

1. 1
   温度the reaction mixture was heated
2. 2
   温度at reflux overnight
3. 3
   温度After cooling
4. 4
   濃縮the mixture was concentrated
5. 5
   workup.ADDITIONthe residue diluted with ice water (20 ml)
6. 6
   抽出The aqueous phase was extracted with ethyl acetate (4×25 ml) and dichloromethane (4×50 ml)
7. 7
   洗浄the combined organic layers washed with aqueous sodium bicarbonate (15 ml) and brine (15 ml)
8. 8
   乾燥dried over sodium sulfate
9. 9
   濃縮concentrated
10. 10
    その他those described above under preparation example 6, step 2

実験手順

To a suspension of 1-methoxy-4-methylamino-piperidine-4-carboxylic acid (2.0 g, 10.63 mmol) in methanol (50 ml) at 0-10° C. was added thionyl chloride (2.29 ml, 3.76 g, 31.57 mmol) and the reaction mixture was heated at reflux overnight. After cooling, the mixture was concentrated, the residue diluted with ice water (20 ml) and neutralised with aqueous sodium bicarbonate. The aqueous phase was extracted with ethyl acetate (4×25 ml) and dichloromethane (4×50 ml), the combined organic layers washed with aqueous sodium bicarbonate (15 ml) and brine (15 ml), dried over sodium sulfate and concentrated. Yield: 0.76 g of 1-methoxy-4-methylamino-piperidine-4-carboxylic acid methyl ester (compound P5.4) as a viscous, orange oil. The spectral data of this crude material were identical to those described above under preparation example 6, step 2.

出典