1-(2-Hydroxyethyl)piperazine → HCID 131714478, compound

HRID 638559Notes

Reaction equation

HRID 638559 reaction equation
Br[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[O:9])[CH:4]=1.[OH:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30]>CCOCC.CC(C)=O.CCOCC.O.C(OCC)(=O)C.C(Cl)Cl>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30].[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30].[OH:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:2][C:3]2[O:7][N:6]=[C:5]([C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[O:9])[CH:4]=2)[CH2:22][CH2:21]1

Participants

8

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 444266Maleic AcidHCID 20252673HCID 20252673, compound

Product 1

HCID 131714478HCID 131714478, compoundYield 55%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 21226138Dichloromethane ethylacetateSolventHCID 21584533Acetone diethyletherSolvent

Procedure

A solution of 5.7 g of (5-bromomethylisoxazol-3-yl)-4-fluorophenylmethanone in 100 ml of Et2O was added to a solution of 6.5 g of N-beta-hydroxyethylpiperazine in 400 ml of 25% acetone/Et2O. The resulting mixture was stirred at room temperature for 24 hours. This mixture was filtered and the solution was concentrated in vacuo to give an oil. The residue was dissolved in 300 ml of H2O and shortly thereafter a precipitate formed. The solid was filtered and dried to give 5.2 g of crude solid. A solution of 4.3 g of the amine in 50 ml of 50% ethyl acetate/CH2Cl2 was added dropwise to a solution of excess maleic acid in 600 ml of Et2O. The precipitated salt was filtered and recrystallized from 160 ml of isopropanol to yield 5.2 g (55%) of crystals, m.p. 139°-140°.

Workup

  1. filtrationThis mixture was filtered
  2. concentrationthe solution was concentrated in vacuo
  3. customto give an oil
  4. customshortly thereafter a precipitate formed
  5. filtrationThe solid was filtered
  6. customdried
  7. customto give 5.2 g of crude solid
  8. filtrationThe precipitated salt was filtered
  9. customrecrystallized from 160 ml of isopropanol

Sources & evidence

ORD record
ord-316db3fcc85c4b198b5e54d65845faa8
Source dataset
uspto-grants-1985_12
Patent number
US04562187

Reaction notes

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