2-Bromoanisole → HCID 2729059, compound

HRID 1597269Notes

Reaction equation

HRID 1597269 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].C([Li])CCC.[CH2:15]([N:22]1[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[CH2:15]([N:22]1[CH2:27][CH2:26][C:25]([OH:28])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])[CH2:24][CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 113582-BromoanisoleHCID 192201-Benzyl-4-piperidoneHCID 178418339Butyllithium

Product 1

HCID 2729059HCID 2729059, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-70 °C

Procedure

A solution of 15 g of 2-bromoanisole in 50 ml of THF is cooled to −70° C., under nitrogen, a 1.6 M solution of n-butyllithium in THF is added dropwise and the mixture is kept stirring for 1 hour. The mixture is cooled to −70° C. and a solution of 15.2 g of 1-benzylpiperid-4-one in 50 ml of THF is added dropwise. The mixture is kept stirring while allowing the temperature to rise to RT and after 1 hour, the reaction mixture is concentrated under vacuum. The residue is taken up in AcOEt, the organic phase washed with water, with a saturated solution of NaCl, dried over MgSO4 and the solvent evaporated under vacuum. 14 g of the expected product are obtained after crystallization from the AcOEt/ether/heptane mixture.

Workup

  1. stirringThe mixture is kept stirring
  2. waitto rise to RT and after 1 hour
  3. concentrationthe reaction mixture is concentrated under vacuum
  4. washthe organic phase washed with water, with a saturated solution of NaCl
  5. dry with materialdried over MgSO4
  6. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-fa76b3413d4f46a0ab9d829772969ae5
Source dataset
uspto-grants-2001_09
Patent number
US06294537B1

Reaction notes

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