Chloroacetyl chloride → 2-chloro-N-(1,3,3-trimethylbicyclo[2,2,1]hept-2-yl)acetamide

HRID 51289Notes

Reaction equation

HRID 51289 reaction equation
[CH3:1][C:2]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4]([CH3:10])([CH3:9])[CH:3]2[NH2:11].[Cl:12][CH2:13][C:14](Cl)=[O:15]>C(Cl)Cl.C(N(CC)CC)C>[Cl:12][CH2:13][C:14]([NH:11][CH:3]1[C:4]([CH3:10])([CH3:9])[CH:5]2[CH2:8][C:2]1([CH3:1])[CH2:7][CH2:6]2)=[O:15]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 4184451,3,3-Trimethylbicyclo[2.2.1]heptan-2-amine

Product 1

HCID 222510912-chloro-N-(1,3,3-trimethylbicyclo[2,2,1]hept-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1,3,3-trimethylbicyclo[2.2.1]hept-2-ylamine (5 g, 26.3 mmol) in methylene chloride (20 ml) and triethylamine (4 ml) was added chloroacetyl chloride (2.1 ml, 26.4 mmol) dropwise. The resulting solution was stirred for 12 hours, then the solvent removed under reduced pressure. The residue was partitioned between ethyl acetate and water, the organic layer washed with brine, and dried over magnesium sulfate. The ethyl acetate solution was absorbed onto silica gel, which was eluted with 10% ethyl acetate/hexane, to yield 2-chloro-N-(1,3,3-trimethylbicyclo[2,2,1]hept-2-yl)acetamide as a white solid.

Workup

  1. customthe solvent removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washthe organic layer washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe ethyl acetate solution was absorbed onto silica gel, which
  6. washwas eluted with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e166723ebbaa4739aeb3ed3b4ce9f563
Source dataset
uspto-grants-2004_03
Patent number
US06713650B2

Reaction notes

Loading…