Morpholine → HCID 13690981, compound

HRID 2290781Notes

Reaction equation

HRID 2290781 reaction equation
Cl[CH2:2][C:3]1[N:7]=[C:6]([CH:8]([CH3:22])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[O:5][N:4]=1.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CN(C=O)C>[F:21][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:8]([C:6]1[O:5][N:4]=[C:3]([CH2:2][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:7]=1)[CH3:22]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 136909413-Chloromethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

Product 1

HCID 13690981HCID 13690981, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.52 g of 3-chloromethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole in 30 ml of DMF was added 1.68 g of morpholine. The mixture was allowed to stand at room temperature overnight, then poured into ice-water and extracted with benzene. The organic phase was washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed over silica gel using benzene-ethyl acetate (5:2, v/v) as an eluent to yield 1.83 g of 5-(3-fluoro-4-phenyl-α-methylbenzyl)-3-morpholinomethyl-1,2,4-oxadiazole as an oil. It was crystallized from diisopropyl ether to give colorless needles, m.p. 91.5°-92.5° C.

Workup

  1. extractionextracted with benzene
  2. washThe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-feda91d9402e4e5db25af51d6422b52e
Source dataset
uspto-grants-1986_10
Patent number
US04618617

Reaction notes

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