Methanol → Methyl 2-(piperidin-1-yl)pyridine-4-carboxylate

HRID 1174509노트

반응식

HRID 1174509 반응식
[N:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][N:15]=2)[C:10]([OH:12])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.[CH3:20]O>>[N:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][N:15]=2)[C:10]([O:12][CH3:20])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 64842372-Piperidinoisonicotinic acid

생성물 1

HCID 18525843Methyl 2-(piperidin-1-yl)pyridine-4-carboxylate

반응 조건

온도
0 °C

실험 절차

A mixture of 2-Piperidin-1-yl-isonicotinic acid (30 g, 0.145 mol) in methanol (500 mL) was cooled to 0° C. and then thionylchloride (42 mL) was added. The reaction mixture was refluxed for 20 h. The solvent was removed under vacuum and the residue was taken up in EtOAc (500 mL). The organic layer was washed with 10% aqueous NaHCO3 solution, water, brine and dried. The solvent was removed under vacuum to methyl 2-piperidin-1-ylisonicotinate (18 g, 56%) as yellow liquid.

후처리

  1. temperatureThe reaction mixture was refluxed for 20 h
  2. customThe solvent was removed under vacuum
  3. washThe organic layer was washed with 10% aqueous NaHCO3 solution, water, brine
  4. customdried
  5. customThe solvent was removed under vacuum to methyl 2-piperidin-1-ylisonicotinate (18 g, 56%) as yellow liquid

출처 및 근거

ORD 기록
ord-8b3d10d9494541d18d06923bddbe186d
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838522B2

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