1-(2-Hydroxyethyl)piperazine → HCID 54373614, compound

HRID 1645802Notes

Reaction equation

HRID 1645802 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8](O)=O.S(Cl)(Cl)=O.[N:15]1([CH2:21][CH2:22][OH:23])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1(C)C=CC=CC=1.N1C=CC=CC=1.O1CCCC1.O>[OH:23][CH2:22][CH2:21][N:15]1[CH2:20][CH2:19][N:18]([CH2:8][CH:7]=[CH:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16]1

Participants

9

Reactant 4

HCID 76771-(2-Hydroxyethyl)piperazineHCID 10876Furylacrylic acidHCID 24386Thionyl ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 54373614HCID 54373614, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

5.0 g (0.036 mol) 3-(2-furyl)acrylic acid was suspended in 100 ml toluene, followed by addition of 7.9 ml (0.108 mol) thionyl chloride. The mixture was refluxed for 1 h, cooled, evaporated and the residue stripped twice with toluene. The resulting acylchloride was redissolved in 25 ml toluene and added dropwise to a solution of 4.7 g (0.036 mol) 1-piperazineethanol in 25 ml toluene and 25 ml pyridine. The reaction mixture was stirred at reflux temperature for 1 h, then cooled, diluted with toluene and washed successively with one portion of 1N sodium hydroxide and three portions of water. Evaporation in vacuo left 3.4 g of an amber oil, which was redissolved in 75 ml of tetrahydrofuran and added dropwise to a solution of 1.32 g (0.035 mol) lithium aluminium hydride in 75 ml of tetrahydrofuran. The reaction mixture was stirred at room temperature for 1 h, cooled in an ice bath and hydrolyzed by dropwise addition of water. The precipitate was filtered off and washed with tetrahydrofuran. The filtrate was concentrated in vacuo and the residue redissolved in acetonitrile. A solution of maleic acid in acetonitrile was added and the precipitate collected by filtration. Recrystallization from isopropanol gave the 1-(2-hydroxyethyl)-4-[3-(2-furyl)-2-propenyl]-piperazine as the dimaleate salt, m.p. 165°-67° C.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. temperaturecooled
  3. customevaporated
  4. dissolutionThe resulting acylchloride was redissolved in 25 ml toluene
  5. temperatureat reflux temperature for 1 h
  6. temperaturecooled
  7. washwashed successively with one portion of 1N sodium hydroxide and three portions of water
  8. customEvaporation in vacuo
  9. waitleft 3.4 g of an amber oil, which
  10. dissolutionwas redissolved in 75 ml of tetrahydrofuran
  11. stirringThe reaction mixture was stirred at room temperature for 1 h
  12. filtrationThe precipitate was filtered off
  13. washwashed with tetrahydrofuran
  14. concentrationThe filtrate was concentrated in vacuo
  15. dissolutionthe residue redissolved in acetonitrile
  16. additionA solution of maleic acid in acetonitrile was added
  17. filtrationthe precipitate collected by filtration
  18. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-812255520172463cabc9d864e5ac4de3
Source dataset
uspto-grants-1993_01
Patent number
US05177077

Reaction notes

Loading…