반응 #657284

반응 방정식

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

methanol

thionyl chloride

→

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

반응 조건

후처리

1. 1
   온도the reaction mixture was heated
2. 2
   온도at reflux for 7 days
3. 3
   온도After cooling
4. 4
   농축the mixture was concentrated
5. 5
   workup.ADDITIONthe residue diluted with ice water and neutralised with aqueous sodium bicarbonate
6. 6
   추출The aqueous phase was extracted with ethyl acetate (4×)
7. 7
   세척the combined organic layers washed with brine
8. 8
   건조dried over sodium sulfate
9. 9
   농축concentrated
10. 10
    기타The residue was purified by chromatography on silica gel (gradient ethyl acetate→ethyl acetate/methanol 20:1)

실험 절차

To a suspension of 1-methoxy-4-methylamino-piperidine-4-carboxylic acid hydrochloride salt (2.08 g, 9.26 mmol) in methanol (20 ml) at 0-5° C. was added thionyl chloride (2.41 ml, 3.97 g, 33.40 mmol) and the reaction mixture was heated at reflux for 7 days. After cooling, the mixture was concentrated, the residue diluted with ice water and neutralised with aqueous sodium bicarbonate. The aqueous phase was extracted with ethyl acetate (4×), the combined organic layers washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (gradient ethyl acetate→ethyl acetate/methanol 20:1). Yield: 76 mg of 1-methoxy-4-methylamino-piperidine-4-carboxylic acid methyl ester (title compound P5.4) as an oil.

출처