반응 #2122494

반응 방정식

Acetyl chloride

methanol

4-hydroxy-1-methoxypiperidine-4-carbonitrile

methanol

→

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

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition
2. 2
   기타The cooling was removed
3. 3
   기타the suspension formed
4. 4
   workup.WAITwas left
5. 5
   workup.STIRRINGstirring at room temperature overnight
6. 6
   기타The solvent was evaporated under vacuum
7. 7
   workup.DISSOLUTIONthe residue was dissolved in cold (0° C.) water
8. 8
   workup.ADDITIONNaHCO3 (saturated aqueous solution) was added carefully
9. 9
   추출The aqueous phase was thoroughly extracted three times with ethyl acetate
10. 10
    건조dried over magnesium sulfate
11. 11
    여과filtered
12. 12
    농축concentrated
13. 13
    기타The crude product was used without further purification

실험 절차

Acetyl chloride (40.7 g, 0.52 mol) was added slowly to dry methanol (115 ml) cooled to 0° C. under argon. After the addition, the solution was stirred for an additional ½ hour at 0° C. This solution was then added dropwise into a cold (0° C.) solution of 4-hydroxy-1-methoxypiperidine-4-carbonitrile (5.40 g, 34.6 mmol) in methanol (45 ml). The cooling was removed and the suspension formed was left stirring at room temperature overnight. The solvent was evaporated under vacuum and the residue was dissolved in cold (0° C.) water. NaHCO3 (saturated aqueous solution) was added carefully to adjust the pH to 7. The aqueous phase was thoroughly extracted three times with ethyl acetate. The organic layers were combined, dried over magnesium sulfate, filtered and concentrated. The crude product was used without further purification. Yield: 4.9 g of 4-hydroxy-1-methoxy-piperidine-4-carboxylic acid methyl ester (title compound P4.4) as light yellow oil.

출처