2-Chloronicotinic acid → 2-[4-(2,3-Dihydroxypropyl)piperazin-1-yl]pyridine-3-carboxylic acid

HRID 231766Notes

Reaction equation

HRID 231766 reaction equation
[OH:1][CH:2]([CH2:10][OH:11])[CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Cl[C:13]1[N:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]>O1CCOCC1>[OH:1][CH:2]([CH2:10][OH:11])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:13]2[N:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=[O:16])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 762582-Chloronicotinic acidHCID 1110023-(Piperazin-1-yl)propane-1,2-diol

Product 1

HCID 200320102-[4-(2,3-Dihydroxypropyl)piperazin-1-yl]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Grams 32 of 1-(2,3-dihydroxypropyl)piperazine and 15.7 g of 2-chloronicotinic acid in 500 ml dioxane were refluxed for 8 hours. The reaction mixture was cooled, settled, the solvent separated and removed. The residue was triturated under heating with absolute ethanol and gave 16.2 g of 2-[4-(2,3-dihydroxypropyl)piperazin-1-yl]nicotinic acid melting at 210°-212° C. (with decomposition)

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent separated
  3. customremoved
  4. customThe residue was triturated
  5. temperatureunder heating with absolute ethanol

Sources & evidence

ORD record
ord-2f0badfe41a146dc9ebfbc463ad6b4d4
Source dataset
uspto-grants-1989_07
Patent number
US04849422

Reaction notes

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