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

HRID 2063352Notes

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 vacua 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 vacua
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-c3cb7238cd2745debb754ad33d044f1b
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288383B2

Reaction notes

Loading…