Boron trifluoride → 1-Benzylcyclopropylamine

HRID 1518177Notes

Reaction equation

HRID 1518177 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([Mg]Br)[CH3:11].B(F)(F)F.[OH-].[Na+]>C(OCC)C.C(OCC)(=O)C>[CH2:7]([C:8]1([NH2:9])[CH2:11][CH2:10]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6356Boron trifluorideHCID 8794PhenylacetonitrileHCID 14798Sodium HydroxideHCID 178418443HCID 178418443, compound

Product 1

HCID 1529231-BenzylcyclopropylamineYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of phenylacetonitrile (3 g, 25.61 mmol) and tetraisopropylorthotitanate (8 ml, 27.15 mmol) in diethyl ether (Et2O)/tetrahydrofuran (THF) (1/1, 100 ml) ethyl-magnesiumbromide (49.33 mmol) was added at room temperature. The exothermic mixture was stirred for 1 h at room temperature. Then BF3×Et2O (49.34 mmol) was added and the mixture was stirred for 1 h. The mixture was poured into a cold aqueous solution of NaOH (10%) and diluted with ethyl acetate. The mixture was filtered, and the organic layer was washed with water and brine, dried over MgSO4, filtered, and the solvent evaporated under reduced pressure to give the product as a yellow oil (3.6 g, 96%).

Workup

  1. stirringthe mixture was stirred for 1 h
  2. filtrationThe mixture was filtered
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-db81c2157f224044bbe11b905eb0bd50
Source dataset
uspto-grants-2012_07
Patent number
US08232426B2

Reaction notes

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