Tetrahydrofuran → HCID 19799597, compound

HRID 974573

Reaction equation

HRID 974573 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+].Br.Br.[CH2:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[CH2:28][CH3:29].[O:36]1CCCC1>O.CC(O)C>[C:5]([OH:36])(=[O:6])/[CH:14]=[CH:15]/[C:19]([OH:21])=[O:22].[CH2:27]([N:30]1[CH2:35][CH2:34][N:33]([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])[CH2:32][CH2:31]1)[CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 3085288N-Propylpiperazinium dibromideHCID 197996061-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine

Product 1

HCID 19799597HCID 19799597, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 2.8 g (0.01 mole of 3-[3-(trifluoromethyl) phenoxy]-1-azetidinecarbonyl chloride and 4.2 g (0.03 mole) of potassium carbonate in 25 ml of tetrahydrofuran was stirred for 10 min, then treated with 2.9 g (0.01 mole) of 1-propylpiperazine dihydrobromide in small portions. After 30 min, a few pieces of ice were added. After stirring for 17 hr, the reaction was diluted with 200 ml of water then extracted with methylene chloride (2×50 ml). The combined extracts were dried over magnesium sulfate and concentrated in vacuo, yielding 4.84 g of crude residue. The residue was converted to the fumarate salt in 2-propanol, concentrated to a solid in vacuo and recrystallized from acetone with a trace of ethanol to yield 2.9 g (59.5%) of fine white crystals; m.p 117°-123° C.

Workup

  1. waitAfter 30 min
  2. additiona few pieces of ice were added
  3. stirringAfter stirring for 17 hr
  4. extractionthen extracted with methylene chloride (2×50 ml)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customyielding 4.84 g of crude residue
  8. concentrationconcentrated to a solid in vacuo
  9. customrecrystallized from acetone with a trace of ethanol

Sources & evidence

ORD record
ord-1b26e8713e0641c9b4c07d75148a8592
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Linked notes

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