Allylamine → HCID 22141298, compound

HRID 1826440Notes

Reaction equation

HRID 1826440 reaction equation
Cl[CH2:2][CH:3]1[CH:5]([C:6]([O:8]CC)=O)[C:4]1([CH3:20])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1.[CH2:21]([NH2:24])[CH:22]=[CH2:23]>>[CH2:21]([N:24]1[CH2:2][CH:3]2[CH:5]([C:4]2([CH3:20])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:6]1=[O:8])[CH:22]=[CH2:23]

Participants

3

Reactant 2

HCID 7853AllylamineHCID 22141336Ethyl 3-(chloromethyl)-2-methyl-2-(3-nitrophenyl)cyclopropanecarboxylate

Product 1

HCID 22141298HCID 22141298, compoundYield 100.6%

Procedure

Ethyl 3-(chloromethyl)-2-methyl-2-(3-nitrophenyl)cyclopropanecarboxylate (Preparation 5, 1 g, 3.36 mmol) in allylamine (1.15 g, 20.1 mmol) was heated in a sealed tube at 150° C. for 16 h. After cooling the reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane and washed with saturated aqueous sodium hydrogen carbonate solution. The organic extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product as a yellow oil (0.92 g, 100%).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialThe organic extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4447f71cdad64f729f4a30df0f909a2e
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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