3-Azabicyclo[3.2.2]nonane → N-bromomethylcarbonyl-3-azabicyclo[3.2.2]nonane

HRID 963500Notes

Reaction equation

HRID 963500 reaction equation
[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][NH:3][CH2:2]2.[Br:10][CH2:11][C:12](Br)=[O:13]>ClCCl.O>[Br:10][CH2:11][C:12]([N:3]1[CH2:4][CH:5]2[CH2:8][CH2:9][CH:1]([CH2:7][CH2:6]2)[CH2:2]1)=[O:13]

Participants

5

Reactant 2

HCID 92403-Azabicyclo[3.2.2]nonaneHCID 61147Bromoacetyl bromide

Product 1

HCID 21701395N-bromomethylcarbonyl-3-azabicyclo[3.2.2]nonaneYield 46.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-azabicyclo[3.2.2]nonane (1.25 g) in dichioromethane (20 ml) and water (0.75 ml) was added dropwise a solution of bromoacetyl bromide (2.02 g) in dichloromethane (10 ml) at, 5°-10° C. The mixture was allowed to warm to room temperature and stirred for 1 hour at the same temperature. The reaction mixture was washed with a saturated sodium bicarbonate aqueous solution (10 ml) and a brine (10 ml). The organic layer was dried over magnesium sulfate. Filtration and evaporation gave N-bromomethylcarbonyl-3-azabicyclo[3.2.2]nonane (1.15 g). The compound was used in a following reaction step without further purification.

Workup

  1. washThe reaction mixture was washed with a saturated sodium bicarbonate aqueous solution (10 ml)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-3d824b88633b4b45ae1f2cd160a9c860
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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