Trifluoroacetic acid → 5-[(3,4-Dichlorophenyl)methyl]-2-azabicyclo[2.2.2]octane

HRID 1793640Notes

Reaction equation

HRID 1793640 reaction equation
C(OC([N:8]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]2[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)=O)(C)(C)C.ClCl.C(O)(C(F)(F)F)=O>>[Cl:24][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[Cl:23])[CH2:16][CH:11]1[CH2:10][CH:9]2[CH2:15][CH2:14][CH:12]1[CH2:13][NH:8]2

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24526ChlorineHCID 69593397HCID 69593397, compound

Product 1

HCID 220228245-[(3,4-Dichlorophenyl)methyl]-2-azabicyclo[2.2.2]octaneYield 96.8%

Procedure

To a solution of 5-(3,4-dichloro-benzyl)-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester (0.24 g, 0.65 mmol) in 2 mL of CH2 Cl2 was added 1 mL of TFA. After the mixture was stirred at rt for 1 h, it was quenched with NaHCO3 (sat.). It was then extracted with CH2Cl2 and the organic layer was washed with NaCl (sat.), dried over Na2SO4 and concentrated to give 170 mg of 5-(3,4-Dichloro-benzyl)-2-aza-bicyclo[2.2.2]octane (M++1: 270).

Workup

  1. customit was quenched with NaHCO3 (sat.)
  2. extractionIt was then extracted with CH2Cl2
  3. washthe organic layer was washed with NaCl (sat.)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-44ae9cae3c594257b3e75c823ab048f1
Source dataset
uspto-grants-2006_07
Patent number
US07081531B2

Reaction notes

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