3-(Piperazin-1-yl)propane-1,2-diol → 4-[4-(2,3-Dihydroxypropyl)piperazin-1-yl]pyrimidine-5-carboxylic acid ethyl ester dihydrochloride

HRID 231772Notes

Reaction equation

HRID 231772 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.[CH2:12]([O:14][C:15]([C:17]1[C:18]([Cl:23])=[N:19][CH:20]=[N:21][CH:22]=1)=[O:16])[CH3:13]>O1CCOCC1>[ClH:23].[ClH:23].[CH2:12]([O:14][C:15]([C:17]1[C:18]([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:19][CH:20]=[N:21][CH:22]=1)=[O:16])[CH3:13]

Participants

4

Reactant 2

HCID 1110023-(Piperazin-1-yl)propane-1,2-diolHCID 12684326Ethyl 4-chloropyrimidine-5-carboxylate

Product 1

HCID 678614724-[4-(2,3-Dihydroxypropyl)piperazin-1-yl]pyrimidine-5-carboxylic acid ethyl ester dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Grams 7.4 of 1-(2,3-dihydroxypropyl)piperazine and 4.3 g of 4-chloropyrimidine-5-carboxylic acid ethyl ester were warmed to 90° C. for 45 minutes in 100 ml dioxane. The reaction mixture was then settled, the supernatant liquor evaporated to dryness and the residue dissolved in hydrochloric ethanol and diluted with isopropanol until complete precipitation. By addition of 95° ethanol, the so formed gum crystallized and 4 g of 4-[4-(2,3-dihydroxypropyl)piperazin-1-yl]pyrimidine-5-carboxylic acid ethyl ester dihydrochloride, melting at 190°-193° C. (with decomposition), were obtained.

Workup

  1. customthe supernatant liquor evaporated to dryness
  2. dissolutionthe residue dissolved in hydrochloric ethanol
  3. additiondiluted with isopropanol until complete precipitation
  4. additionBy addition of 95° ethanol
  5. customthe so formed gum crystallized

Sources & evidence

ORD record
ord-456c26e5656e48b5be33bab1ac5493e5
Source dataset
uspto-grants-1989_07
Patent number
US04849422

Reaction notes

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