2-Bromoisonicotinic acid → 2-Piperidinoisonicotinic acid

HRID 1174508Notes

Reaction equation

HRID 1174508 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6]>N1CCCCC1>[N:10]1([C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=2)[C:5]([OH:7])=[O:6])[CH2:9][CH2:8][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 2227012-Bromoisonicotinic acid

Product 1

HCID 64842372-Piperidinoisonicotinic acidYield 171.4%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 2-bromoisonicotinic acid (40 g, 0.198 mol) and piperidine (200 mL) was refluxed at 105° C. for 24 h under N2 atmosphere. The excess piperidine was distilled under vacuum and crude residue was diluted with water (500 mL) and extracted with chloroform (3×250 mL), washed with brine and dried. The solvent was removed under vacuum to give 2-Piperidin-1-yl-isonicotinic acid (35 g, 85%) as a solid.

Workup

  1. distillationThe excess piperidine was distilled under vacuum and crude residue
  2. additionwas diluted with water (500 mL)
  3. extractionextracted with chloroform (3×250 mL)
  4. washwashed with brine
  5. customdried
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-51751358b2ef49a2bf13cf036dbc2743
Source dataset
uspto-grants-2010_11
Patent number
US07838522B2

Reaction notes

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