Morpholine → HCID 13537607, compound

HRID 638558Notes

Reaction equation

HRID 638558 reaction equation
Br[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[O:9])[CH:4]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>CCOCC.CC(C)=O.CCOCC>[N:17]1([CH2:2][C:3]2[O:7][N:6]=[C:5]([C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[O:9])[CH:4]=2)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 20252673HCID 20252673, compound

Product 1

HCID 13537607HCID 13537607, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 21584533Acetone diethyletherSolvent

Procedure

A solution of 4.5 g of (5-bromomethylisoxazol-3-yl-4-fluorophenylmethanone in 100 ml of Et2O was added dropwise to a solution of 7 ml of morpholine in 300 ml of 50% acetone/Et2O. The resulting mixture was stirred at room temperature for 20 hours. This mixture was filtered and the volatiles evaporated to give a residue which was dissolved in 600 ml of Et2O. The organic solution was washed with water until it became neutral and then with saturated NaCl, and dried over Na2SO4 and concentrated in vacuo to give 4.3 g of a crystalline solid. A 3.6 g sample of the amine was recrystallized from 65 ml of 8% toluene/hexane to yield 2.4 g (64%) of crystals, m.p. 72°-74°.

Workup

  1. filtrationThis mixture was filtered
  2. customthe volatiles evaporated
  3. customto give a residue which
  4. washThe organic solution was washed with water until it
  5. dry with materialwith saturated NaCl, and dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ecc9e8f96ba43c2bb845562fd97d307
Source dataset
uspto-grants-1985_12
Patent number
US04562187

Reaction notes

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