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

HRID 1174509Notes

Reaction equation

HRID 1174509 reaction equation
[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

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 64842372-Piperidinoisonicotinic acid

Product 1

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

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8b3d10d9494541d18d06923bddbe186d
Source dataset
uspto-grants-2010_11
Patent number
US07838522B2

Reaction notes

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