Ethyl 4-oxo-1-piperidinecarboxylate → HCID 14770818, compound

HRID 1090409Notes

Reaction equation

HRID 1090409 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([Br:9])=[CH:4][C:3]=1[F:10].C([Li])CCC.[CH2:16]([O:18][C:19]([N:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1)=[O:20])[CH3:17]>C(OCC)C.CCCCCC>[Br:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([C:24]2([OH:27])[CH2:23][CH2:22][N:21]([C:19]([O:18][CH2:16][CH3:17])=[O:20])[CH2:26][CH2:25]2)=[C:3]([F:10])[CH:4]=1

Participants

6

Reactant 3

HCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 675961,4-Dibromo-2,5-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 14770818HCID 14770818, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-50 °C

Procedure

A solution of 16.55 g (60.85 mmol) 1,4-dibromo-2,5-difluorobenzene in 400 ml of ethyl ether stirred at -75° C. under an argon atmosphere was treated dropwise with 24.3 ml of 2.5 M n-butyl lithium in hexane. The mixture was let warm to -50° C. and treated dropwise with a solution of 11.00 g (64.33 mmol) 1-ethoxycarbonyl-4-piperidone in 100 ml ethyl ether. After stirring a further 0.25 hour, the mixture was let warm to room temperature and extracted with ammonium chloride solution. The organic layer was dried (MgSO4), evaporated and the crude product chromatographed on a silica gel column and crystallized from toluene hexane to afford the title compound, mp 133°-136° C.

Workup

  1. temperaturethe mixture was let warm to room temperature
  2. extractionextracted with ammonium chloride solution
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. customthe crude product chromatographed on a silica gel column
  6. customcrystallized from toluene hexane

Sources & evidence

ORD record
ord-e3305e39836043779a4c8bdea71f1ec0
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

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