Tetrahydrofuran → HCID 19799591, compound

HRID 2081473Notes

Reaction equation

HRID 2081473 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[O:5][CH:6]1[CH2:9][N:8]([C:10](Cl)=[O:11])[CH2:7]1.[CH2:17]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:30](=[O:33])([O-:32])[O-].[K+].[K+].[O:36]1CCCC1>O>[C:4]([OH:36])(=[O:5])/[CH:13]=[CH:14]/[C:30]([OH:32])=[O:33].[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[O:5][CH:6]1[CH2:9][N:8]([C:10]([N:27]2[CH2:28][CH2:29][N:24]([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:25][CH2:26]2)=[O:11])[CH2:7]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 759941-BenzylpiperazineHCID 15042235HCID 15042235, compound

Product 1

HCID 19799591HCID 19799591, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 2.8 g (0.01 mole) of crude 3-(3,4-dichlorophenoxy)-1-azetidinecarbonyl chloride in 25 ml of tetrahydrofuran was treated with 1.8 g (0.01 mole) of 1-benzylpiperazine then with 1.4 g (0.01 mole) of potassium carbonate. After stirring for 30 min, approximately 2 g of ice was added and stirring continued for 18 hr. The reaction mixture was diluted with 200 ml of water. After stirring for 24 hr, the oil which separated had solidified and was collected by filtration (4.8 g). The solid, dissolved in 20 ml of isopropanol, was treated with 1.16 g of fumaric acid dissolved in 25 ml of boiling isopropanol. Upon cooling, the precipitate was collected to yield 2.4 g (55%) of fine white crystalline product, m.p. 193°-195° C.

Workup

  1. stirringstirring
  2. waitcontinued for 18 hr
  3. stirringAfter stirring for 24 hr
  4. customthe oil which separated
  5. filtrationwas collected by filtration (4.8 g)
  6. dissolutionThe solid, dissolved in 20 ml of isopropanol
  7. additionwas treated with 1.16 g of fumaric acid
  8. dissolutiondissolved in 25 ml of boiling isopropanol
  9. temperatureUpon cooling
  10. customthe precipitate was collected

Sources & evidence

ORD record
ord-93eb46c4ce644b8d80f037b65564569e
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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