Morpholine → (2,2-Diphenylbenzo[d][1,3]dioxol-5-yl)(morpholino)methanone

HRID 2184119Notes

Reaction equation

[C:1]1([C:7]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:11][C:10]3[CH:12]=[CH:13][C:14]([C:16](ON4C5C=CC=CC=5N=N4)=[O:17])=[CH:15][C:9]=3[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>C(#N)C>[C:1]1([C:7]2([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[O:11][C:10]3[CH:12]=[CH:13][C:14]([C:16]([N:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)=[O:17])=[CH:15][C:9]=3[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a mixture of 1H-benzotriazol-1-yl 2,2-diphenyl-1,3-benzodioxole-5-carboxylate (300 mg, 0.689 mmol) in acetonitrile (2.0 mL) was added morpholine (100 mg, 1.15 mmol, 1.67 eq.) at 0° C. After 10 min, the cooling bath was removed and the reaction was stirred 3 h at 20° C. The reaction was partitioned between water and dichloromethane. The aqueous layer was extracted with dichloromethane. The combined organic layer was washed with brine and water and then dried in vacuo, affording the title compound (267 mg, quant.) as a white solid.

Workup

customthe cooling bath was removed
customThe reaction was partitioned between water and dichloromethane
extractionThe aqueous layer was extracted with dichloromethane
washThe combined organic layer was washed with brine and water
customdried in vacuo

Sources & evidence

ORD record: ord-f6360b9fb3464a18858b0f13abad46f8
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900227B2

Reaction notes

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