2-Chloroethyl chloroformate → 2-(5-Phenyl-1,2,4-oxadiazol-3-yl)morpholine hydrochloride

HRID 1896176Notes

Reaction equation

C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:16][N:15]=2)[CH2:9]1)C1C=CC=CC=1.[Cl:25]C(OCCCl)=O>ClCCCl>[ClH:25].[C:19]1([C:17]2[O:16][N:15]=[C:14]([CH:10]3[O:11][CH2:12][CH2:13][NH:8][CH2:9]3)[N:18]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 4-benzyl-2-(5-phenyl-1,2,4-oxadiazol-3-yl)morpholine (intermediate 27, 900 mg, 2.80 mmol) in 1,2-dichloroethane (2.0 ml) was added chloroethyl chloroformate (0.46 ml, 4.20 mmol), and the reaction mixture was stirred at 70° C. for 4 hours. The reaction mixture was concentrated in vacuo. After removal of the solvent, the residue was dissolved in methanol (2.0 ml), and the solution was stirred under reflux for one hour. When the reaction was complete (checked by thin layer chromatography), the reaction mixture was concentrated in vacuo. The resulting 2-(5-phenyl-[1,2,4]oxadiazol-3-yl)-morpholine hydrochloride (intermediate 28) was used for next reaction without further purification.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customAfter removal of the solvent
dissolutionthe residue was dissolved in methanol (2.0 ml)
stirringthe solution was stirred
temperatureunder reflux for one hour
concentrationthe reaction mixture was concentrated in vacuo
customThe resulting 2-(5-phenyl-[1,2,4]oxadiazol-3-yl)-morpholine hydrochloride (intermediate 28) was used for next reaction without further purification

Sources & evidence

ORD record: ord-f12cdea224d1460d9fa98a09d1e847d5
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518939B2

Reaction notes

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