Hydrochloric Acid → (4-Fluorophenyl)[2-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-4-morpholinyl]methanone

HRID 1661185Notes

Reaction equation

HRID 1661185 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]=[C:12]([CH:14]3[O:19][CH2:18][CH2:17][NH:16][CH2:15]3)[O:11][N:10]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[F:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1.Cl>ClCCl>[F:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([N:16]2[CH2:17][CH2:18][O:19][CH:14]([C:12]3[O:11][N:10]=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=4)[N:13]=3)[CH2:15]2)=[O:33])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 66618331HCID 66618331, compound

Product 1

HCID 11303234(4-Fluorophenyl)[2-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-4-morpholinyl]methanoneYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-[3-(4-fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-morpholine hydrochloride (0.15 g, 0.53 mmol) in anhydrous dichloromethane (6 mL), under nitrogen atmosphere, triethylamine (155 mL, 1.1 mmol) and 4-fluorobenzoyl chloride (62 mL, 0.53 mmol) were subsequently added at 0° C. The reaction mixture was allowed to warm at room temperature and stirred overnight. HCl 1N (6 mL) was added and the phases were separated. The organic layer was washed sequentially with HCl 1N (6 mL), NaOH 1N (6 mL×2 times) and with water, then was dried over sodium sulphate and evaporated under reduced pressure. The crude was purified by flash chromatography (silica gel, eluent: hexane/ethyl acetate 7/3) to afford 120 mg of (4-fluoro-phenyl)-{2-[3-(4-fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-morpholin-4-yl}-methanone as a white solid.

Workup

  1. customthe phases were separated
  2. washThe organic layer was washed sequentially with HCl 1N (6 mL), NaOH 1N (6 mL×2 times) and with water
  3. dry with materialwas dried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customThe crude was purified by flash chromatography (silica gel, eluent: hexane/ethyl acetate 7/3)

Sources & evidence

ORD record
ord-657c614ce418459698bdc2a2ca593e3a
Source dataset
uspto-grants-2011_10
Patent number
US08030331B2

Reaction notes

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