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

HRID 890505Notes

Reaction equation

HRID 890505 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. B. Preparation of a Compound of Formula (1) in which R1 is Cyclohexyl and R2 is Phenyl

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-b9120ec755604049aec9591f8510cbb9
Source dataset
uspto-grants-2006_02
Patent number
US06995285B2

Reaction notes

Loading…