Ammonium Hydroxide → 3-(4-Fluorophenoxy)-1-azetidinecarboxamide

HRID 2081443Notes

Reaction equation

HRID 2081443 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]2)=[CH:4][CH:3]=1.[OH-].[NH4+:17]>O1CCCC1>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11]([NH2:17])=[O:12])[CH2:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 150533673-(4-Fluorophenoxy)-1-azetidinecarbonyl chloride

Product 1

HCID 150534383-(4-Fluorophenoxy)-1-azetidinecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.52 g (0.022 mole) of crude 3-(4-fluorophenoxy)-1-azetidine carbonyl chloride in 20 ml of tetrahydrofuran was treated with 10 ml of concentrated ammonium hydroxide while stirring. The exothermic reaction mixture was stirred for 18 hr as it cooled to ambient temperature. The reaction mixture was diluted with 400 ml of ice water to produce a phase separation. Upon standing, the oily phase solidified and was collected by filtration yielding 12.5 g of crude wet product. Recrystallization from aqueous ethanol after charcoal treatment produced an oil which slowly crystallized. The sample was recrystallized from methylene chloride, yield 1.6 g (35%) of amorphous-like powder, m.p. 185°-188° C.

Workup

  1. stirringThe exothermic reaction mixture was stirred for 18 hr as it
  2. customto produce
  3. customa phase separation
  4. filtrationthe oily phase solidified and was collected by filtration
  5. customyielding 12.5 g of crude wet product
  6. customRecrystallization from aqueous ethanol after charcoal treatment
  7. customproduced an oil which
  8. customslowly crystallized
  9. customThe sample was recrystallized from methylene chloride, yield 1.6 g (35%) of amorphous-like powder, m.p. 185°-188° C.

Sources & evidence

ORD record
ord-e7427bec8d3f4f6db73f0056242c5f57
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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