3-Fluorobenzyl chloride → HCID 10308820, compound

HRID 1349392Notes

Reaction equation

HRID 1349392 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:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Cl>CN(C)C=O>[CH2:1]([C:8]1([N:15]([CH3:16])[CH3:17])[CH2:13][CH2:12][CH:11]([O:14][CH2:28][C:27]2[CH:30]=[CH:31][CH:32]=[C:25]([F:24])[CH:26]=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 99743-Fluorobenzyl chlorideHCID 21093239HCID 21093239, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10308820HCID 10308820, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.65 g of 4-benzyl-4-dimethylaminocyclohexanol were dissolved in 20 ml of dimethylformamide; 1.40 g of potassium tert.-butoxide were added and stirring was carried out for 45 minutes, before 2.0 g of 3-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 (3.69 g) was separated on silica gel with hexane/ethyl acetate (V:V=1:1). 1.96 g of [1-benzyl-4-(3-fluoro-benzyloxy)-cyclohexyl]dimethylamine were obtained and, as described for Example 1, were converted into 1.13 g 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 (3.69 g) was separated on silica gel with hexane/ethyl acetate (V:V=1:1)

Sources & evidence

ORD record
ord-42144170bdee4c82b0bbe8422647c903
Source dataset
uspto-grants-2007_05
Patent number
US07211694B2

Reaction notes

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