Hydrochloric Acid → 1-(1-Benzylamino-1-cyanomethyl)-1-ethoxycarbonylcyclopropane

HRID 324690

Reaction equation

HRID 324690 reaction equation
[C-:1]#[N:2].[K+].[CH2:4]([NH2:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:12]([C:14]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]1)=O.Cl>O.C(O)C>[CH2:4]([NH:11][CH:12]([C:14]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]1)[C:1]#[N:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 9032Potassium CyanideHCID 9964122Ethyl 1-formylcyclopropanecarboxylate

Product 1

HCID 153910461-(1-Benzylamino-1-cyanomethyl)-1-ethoxycarbonylcyclopropaneYield 87.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

An eggplant type flask was charged with 131 mg of potassium cyanide and 539 mg of benzylamine, and the contents were dispersed in 1 ml of water. Thereto was added dropwise 146 mg of ethyl 1-formylcyclopropane-1-carboxylate dissolved in 2 ml of ethanol at room temperature, followed by dropwise addition of 0.2 ml of concentrated hydrochloric acid. The reaction solution was stirred for 2.5 hours at 50° C. After confirming completion of the reaction, the reaction solution was mixed with ice water and extracted with ethyl acetate. Next, the resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and, after removing insoluble matter by filtration, concentrated under a reduced pressure. Thereafter, the resulting residue was subjected to a silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 231 mg (87%) of the title compound in the form of colorless oil.

Workup

  1. customcompletion of the reaction
  2. extractionextracted with ethyl acetate
  3. washNext, the resulting organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customafter removing insoluble matter
  6. filtrationby filtration
  7. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-58070d59708343a6b8b526198dd53907
Source dataset
uspto-grants-2001_04
Patent number
US06218548B1

Linked notes

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