Benzyl Bromide → HCID 12718203, compound

HRID 2111607Notes

Reaction equation

HRID 2111607 reaction equation
[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH2:24]([N:5]1[CH2:6][CH2:7][C:2]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)([OH:1])[CH2:3][CH2:4]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 752554-[3-(Trifluoromethyl)phenyl]-4-piperidinol

Product 1

HCID 12718203HCID 12718203, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 24.5 g of 4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidine (commercial) and 27.6 g of K2CO3 in 20 ml of DMF is added dropwise, at rt, 17.1 g of benzyl bromide, and the mixture is then heated at 40° C. for 2 hours and stirred overnight at rt. The reaction mixture is concentrated under vacuum, the residue is taken up in water and extracted with EtOAc, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. 31 g of the expected product are obtained.

Workup

  1. additionis added dropwise, at rt
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. extractionextracted with EtOAc
  4. washthe organic phase is washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-7d76844d2cf0425e8ea9b3fe550f3e5d
Source dataset
uspto-grants-2009_04
Patent number
US07521449B2

Reaction notes

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