Benzyl Chloride → 1-{8-[Benzyl(methyl)amino]-3-azabicyclo[3.2.1]oct-3-yl]-2,2,2-trifluoro-1-ethanone

HRID 411547Notes

Reaction equation

HRID 411547 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([N:5]1[CH2:11][CH:10]2[CH:12]([NH:13][CH3:14])[CH:7]([CH2:8][CH2:9]2)[CH2:6]1)=[O:4].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC#N>[CH2:17]([N:13]([CH3:14])[CH:12]1[CH:10]2[CH2:9][CH2:8][CH:7]1[CH2:6][N:5]([C:3](=[O:4])[C:2]([F:16])([F:1])[F:15])[CH2:11]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 185409162,2,2-Trifluoro-1-[8-(methylamino)-3-azabicyclo[3.2.1]oct-3-yl]-1-ethanone

Product 1

HCID 185409031-{8-[Benzyl(methyl)amino]-3-azabicyclo[3.2.1]oct-3-yl]-2,2,2-trifluoro-1-ethanoneYield 42.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2,2,2-trifluoro-1-[8-(methylamino)-3-azabicyclo[3.2.1]oct-3-yl]-1-ethanone (see step (v) above; 4.5 g, 16 mmol), benzylchloride (3.0 g, 16 mmol) and TEA (6.6 mL) in MeCN (50 mL) was stirred at 60° C. overnight. The mixture was evaporated and then DCM and water were added. The organic phase was washed with NaHCO3 solution, dried (Na2SO4) and then evaporated. The resulting crude product was purified by chromatography on silica gel (DCM eluant) to give 2.2 g (42%) of the sub-title compound.

Workup

  1. customThe mixture was evaporated
  2. additionDCM and water were added
  3. washThe organic phase was washed with NaHCO3 solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe resulting crude product was purified by chromatography on silica gel (DCM eluant)

Sources & evidence

ORD record
ord-f69a2e1c55ec4e0a82eb4afc97c423e3
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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