Piperidine → Benzyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate

HRID 1623665Notes

Reaction equation

HRID 1623665 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].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.[CH2:53]([O:60][C:61]1[CH:76]=[CH:75][C:74](Br)=[CH:73][C:62]=1[C:63]([O:65][CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)=[O:64])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.[NH:78]1[CH2:83][CH2:82][CH2:81][CH2:80][CH2:79]1>CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[C:54]1([CH2:53][O:60][C:61]2[CH:76]=[CH:75][C:74]([N:78]3[CH2:83][CH2:82][CH2:81][CH2:80][CH2:79]3)=[CH:73][C:62]=2[C:63]([O:65][CH2:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)=[O:64])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

8

Reactant 4

HCID 8082PiperidineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoate

Product 1

HCID 66990101Benzyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Caesium carbonate (689 mg, 2.11 mmol) was finely ground in a nitrogen-filled glovebox and weighed into an oven-dried Schlenk flask. The flask was quickly capped with a rubber septum and purged with argon. Pd2(dba)3 (3.46 mg, 3.78 μmol) and BINAP (7.05 mg, 0.01 mmol) were added into the flask, followed by benzyl 2-(benzyloxy)-5-bromobenzoate (may be prepared as described in Description 4; 600 mg, 1.51 mmol), piperidine (129 mg, 1.510 mmol), and toluene (10 ml). The solution was refluxed for 10 h. The solution was then cooled to room temperature, diluted with ether, filtered, and concentrated in vacuo to yield the title compound.

Workup

  1. additionfilled glovebox
  2. customweighed into an oven-dried Schlenk flask
  3. customThe flask was quickly capped with a rubber septum
  4. custompurged with argon
  5. temperatureThe solution was refluxed for 10 h
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed8b03a1c299454fbb1e181f4c9ebc74
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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