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

HRID 1896172Notes

Reaction equation

C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:15]=2)[CH2:9]1)C1C=CC=CC=1.[Cl:25]C(OCCCl)=O>ClCCCl>[ClH:25].[C:19]1([C:16]2[N:15]=[C:14]([CH:10]3[O:11][CH2:12][CH2:13][NH:8][CH2:9]3)[O:18][N:17]=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-(3-phenyl-1,2,4-oxadiazol-5-yl)morpholine (intermediate 21, 2.0 g, 6.22 mmol) in 1,2-dichloroethane (10 ml) was added chloroethyl chloroformate (2.0 ml, 18.7 mmol), and the reaction mixture was stirred for at 70° C.4 hours. The reaction mixture was concentrated in vacuo. After removal of the solvent, the residue was dissolved in methanol (10 ml), and the reaction solution was stirred for one hour under reflux. When the reaction was complete (checked by thin layer chromatography), the reaction mixture was concentrated in vacuo. The resulting 2-(3-phenyl-[1,2,4]oxadiazol-5-yl)-morpholine hydrochloride (intermediate 22) was used for next reaction without further purification.

Workup

custom4 hours
concentrationThe reaction mixture was concentrated in vacuo
customAfter removal of the solvent
dissolutionthe residue was dissolved in methanol (10 ml)
stirringthe reaction solution was stirred for one hour
temperatureunder reflux
concentrationthe reaction mixture was concentrated in vacuo
customThe resulting 2-(3-phenyl-[1,2,4]oxadiazol-5-yl)-morpholine hydrochloride (intermediate 22) was used for next reaction without further purification

Sources & evidence

ORD record: ord-8f5419b0476449dbab5a010de1ae0e18
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518939B2

Reaction notes

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