3-(Piperazin-1-yl)propane-1,2-diol → 3-[4-(2,3-Dihydroxypropyl)piperazin-1-yl]pyrazine-2-carboxylic acid methyl ester dihydrochloride

HRID 231777Notes

Reaction equation

HRID 231777 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.[CH3:12][O:13][C:14]([C:16]1[C:21]([Cl:22])=[N:20][CH:19]=[CH:18][N:17]=1)=[O:15]>O1CCOCC1>[ClH:22].[ClH:22].[CH3:12][O:13][C:14]([C:16]1[C:21]([N:7]2[CH2:8][CH2:9][N:4]([CH2:3][CH:2]([OH:1])[CH2:10][OH:11])[CH2:5][CH2:6]2)=[N:20][CH:19]=[CH:18][N:17]=1)=[O:15]

Participants

4

Reactant 2

HCID 1110023-(Piperazin-1-yl)propane-1,2-diolHCID 1519497Methyl 3-chloropyrazine-2-carboxylate

Product 1

HCID 678617893-[4-(2,3-Dihydroxypropyl)piperazin-1-yl]pyrazine-2-carboxylic acid methyl ester dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Grams 20.5 of 1-(2,3-dihydroxypropyl)piperazine and 11 g of 3-chloropyrazine-2-carboxylic acid methyl ester in 100 ml dioxane were refluxed for one hour. The reaction mixture was cooled and settled, the solvent evaporated and the obtained residue dissolved in concentrated hydrochloric acid and the solution diluted with isopropanol until incipient precipitation. After resting, 12.7 g of 3-[4-(2,3-dihydroxypropyl)piperazin-1-yl]pyrazine-2-carboxylic acid methyl ester dihydrochloride melting at 195°-197° C. (with decomposition), were obtained.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent evaporated
  3. dissolutionthe obtained residue dissolved in concentrated hydrochloric acid
  4. additionthe solution diluted with isopropanol until incipient precipitation

Sources & evidence

ORD record
ord-3379b5f1f1cf4f3ba8ffe7ee21144da1
Source dataset
uspto-grants-1989_07
Patent number
US04849422

Reaction notes

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