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

HRID 2184119
Notes
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Reaction equation

HRID 2184119 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 8083MorpholineHCID 115901781H-benzotriazol-1-yl 2,2-diphenyl-1,3-benzodioxol-5-carboxylate

Product 1

HCID 10452791(2,2-Diphenylbenzo[d][1,3]dioxol-5-yl)(morpholino)methanoneYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. customthe cooling bath was removed
  2. customThe reaction was partitioned between water and dichloromethane
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washThe combined organic layer was washed with brine and water
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes