4-Fluorobenzyl chloride → HCID 10236866, compound

HRID 1349393Notes

Reaction equation

HRID 1349393 reaction equation
[CH2:1]([C:8]1([N:15]([CH3:17])[CH3:16])[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1>CN(C)C=O>[CH2:1]([C:8]1([N:15]([CH3:16])[CH3:17])[CH2:13][CH2:12][CH:11]([O:14][CH2:29][C:28]2[CH:31]=[CH:32][C:25]([F:24])=[CH:26][CH:27]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 96024-Fluorobenzyl chlorideHCID 21093239HCID 21093239, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10236866HCID 10236866, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.00 g of 4-benzyl-4-dimethylaminocyclohexanol were dissolved in 20 ml of dimethylformamide; 1.06 g of potassium tert.-butoxide were added and stirring was carried out for 45 minutes, before 1.36 g of 4-fluorobenzyl chloride were added dropwise in the course of 30 minutes. After stirring overnight, the mixture was added to 25 ml of ice-water and extracted repeatedly with ethyl acetate. The combined extracts were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The resulting crude product (2.78 g) was separated on silica gel with hexane/ethyl acetate (V:V=1:1). 1.58 g of [1-benzyl-4-(4-fluorobenzyloxy)cyclohexyl]dimethylamine were obtained and, as described for Example 1, were converted into 890 mg of the corresponding hydrochloride using chlorotrimethylsilane and water in 2-butanone (white solid).

Workup

  1. additionwere added dropwise in the course of 30 minutes
  2. stirringAfter stirring overnight
  3. extractionextracted repeatedly with ethyl acetate
  4. washThe combined extracts were washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude product (2.78 g) was separated on silica gel with hexane/ethyl acetate (V:V=1:1)

Sources & evidence

ORD record
ord-c5090b7786d24b038733342dab8f4abe
Source dataset
uspto-grants-2007_05
Patent number
US07211694B2

Reaction notes

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