Tetrahydrofuran → HCID 19799632, compound

HRID 1886682Notes

Reaction equation

HRID 1886682 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]1.[C:19](=[O:22])([O-:21])[O-].[K+].[K+].[CH3:25][N:26]1[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[O:33]1CCCC1>O>[C:5]([OH:33])(=[O:6])/[CH:14]=[CH:15]/[C:19]([OH:21])=[O:22].[CH3:25][N:26]1[CH2:32][CH2:31][CH2:30][N:29]([C:11]([N:9]2[CH2:10][CH:7]([O:6][C:5]3[CH:14]=[CH:15][CH:16]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=3)[CH2:8]2)=[O:12])[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 2283491-MethylhomopiperazineHCID 197996061-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine

Product 1

HCID 19799632HCID 19799632, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 2.8 g (0.01 mole) of 3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride and 1.4 g (0.01 mole) of potassium carbonate in 20 ml of tetrahydrofuran was treated with 1.15 g (0.01 mole) of 1-methylhomopiperazine, and after stirring for 15 minutes a small piece of ice was added. After stirring for 15 hr, the reaction mixture was diluted with 200 ml of water and the oil which separated was extracted into methylene chloride (2×50 ml). The combined extracts were dried over magnesium sulfate and concentrated in vacuo. The residue (3.8 g) was treated with 1.2 g of fumaric acid and dissolved in 20 ml of isopropanol by heating. Upon cooling, the precipitated solid was collected by filtration to yield 4.1 g (86.6%) of white crystals, m.p. 131°-133° C.

Workup

  1. additionwas added
  2. stirringAfter stirring for 15 hr
  3. customthe oil which separated
  4. extractionwas extracted into methylene chloride (2×50 ml)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. additionThe residue (3.8 g) was treated with 1.2 g of fumaric acid
  8. dissolutiondissolved in 20 ml of isopropanol
  9. temperatureby heating
  10. temperatureUpon cooling
  11. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-54aaa51afa354df08de40494099f00a8
Source dataset
uspto-grants-1992_09
Patent number
US05151418

Reaction notes

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