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

HRID 1174509ノート

反応式

HRID 1174509 の反応式
[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

参加物

4

反応物 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 64842372-Piperidinoisonicotinic acid

生成物 1

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

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8b3d10d9494541d18d06923bddbe186d
出典データセット
uspto-grants-2010_11
特許番号
US07838522B2

反応ノート

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