Chloroacetyl chloride → N-chloromethylcarbonyl-2-azatricyclo-[4.3.1.14,8]undecane

HRID 963468Notes

Reaction equation

HRID 963468 reaction equation
[CH:1]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3][NH:2]1)[CH2:9]2.[Cl:12][CH2:13][C:14](Cl)=[O:15]>ClCCl.O>[Cl:12][CH2:13][C:14]([N:2]1[CH2:3][CH:4]2[CH2:10][CH:8]3[CH2:7][CH:6]([CH2:11][CH:1]1[CH2:9]3)[CH2:5]2)=[O:15]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 322724-Azatricyclo[4.3.1.13,8]undecane

Product 1

HCID 86752745N-chloromethylcarbonyl-2-azatricyclo-[4.3.1.14,8]undecaneYield 73.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-azatricyclo[4.3.1.14,8 ]undecane (0.30 g) in dichloromethane (4 ml) and water (0.4 ml) was added dropwise a solution of chloroacetyl chloride (0.26 g) in dichloromethane (2 ml) under stirring at cooling in an ice-bath. The mixture was stirred 2 hours under the same condition and then at ambient temperature overnight. The reaction mixture was washed with IN hydrochloric acid aqueous solution and saturated sodium bicarbonate aqueous solution, and dried over sodium sulfate. Removal of the solvent gave N-chloromethylcarbonyl-2-azatricyclo-[4.3.1.14,8 ]undecane (0.33 g), which was used in a following reaction step without further purification.

Workup

  1. temperatureat cooling in an ice-bath
  2. stirringThe mixture was stirred 2 hours under the same condition
  3. customat ambient temperature
  4. customovernight
  5. washThe reaction mixture was washed with IN hydrochloric acid aqueous solution and saturated sodium bicarbonate aqueous solution
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-a7e93a5b3fce459cbea1916f2deb3d7a
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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