Benzylamine → 1-(1-Benzylamino-1-cyanomethyl)-1-ethoxycarbonylcyclopropane

HRID 849666Notes

Reaction equation

HRID 849666 reaction equation
[CH:1]([C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1)=O.S([O-])(O)=O.[Na+].[C-:16]#[N:17].[K+].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C.O>[CH2:19]([NH:26][CH:1]([C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1)[C:16]#[N:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 9032Potassium CyanideHCID 9964122Ethyl 1-formylcyclopropanecarboxylateHCID 23665763Sodium Bisulfite

Product 1

HCID 153910461-(1-Benzylamino-1-cyanomethyl)-1-ethoxycarbonylcyclopropaneYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

An eggplant type flask was charged with 501 mg of ethyl 1-formylcyclopropane-1-carboxylate and 2 ml of water to which were further added 1.13 g of sodium hydrogen sulfite and 345 mg of potassium cyanide. Thereto was added dropwise 564 mg of benzylamine dissolved in 5 ml of ethanol at room temperature, followed by 2.5 hours of stirring the reaction solution 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 magnesium 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=3:1) to obtain 717 mg (79%) of the title compound in the form of colorless oil. Spectrum data of the thus obtained oily product coincided with those of the compound of Inventive Example 2.

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 magnesium sulfate
  5. customafter removing insoluble matter
  6. filtrationby filtration
  7. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-eeb04ee6567245c5b3e75c2d2b7f8a4a
Source dataset
uspto-grants-2000_01
Patent number
US06013806

Reaction notes

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