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Morpholine → HCID 57318086, compound

HRID 991586
Notes
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Reaction equation

HRID 991586 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6](Br)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2][CH3:3].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([C:4]1[CH:5]=[C:6]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2][CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 18414640HCID 18414640, compound

Product 1

HCID 57318086HCID 57318086, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst
HCID 634876
Binap, (A+-)-
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-propyl-4-benzyloxy-1-bromobenzene (1.0 g, 3.3 mmol), morpholine (0.5 g, 6.6 mmol), Pd(OAc)2 (0.036 g, 0.16 mmol), BINAP (0.082 g, 0.132 mmol) and cesium carbonate (1.50 g, 4.62 mmol) in toluene (134 mL) was degassed and purged with nitrogen. The reaction mixture was stirred at 100° C. overnight. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and 10% aqueous citric acid. The organic layer was washed with water and brine. The organic layer was dried over sodium sulfate, filtered and evaporated to an oil. The resulting oil was chromatographed on silica gel, using toluene with 5% ethyl acetate, to afford the title compound (1.03 g)

Workup

  1. custompurged with nitrogen
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custompartitioned between ethyl acetate and 10% aqueous citric acid
  4. washThe organic layer was washed with water and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to an oil
  8. customThe resulting oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-769476b2fe854e0ab47b645ffb436bc6
Source dataset
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06465497B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes