Phenylacetonitrile → 1-Benzylcyclopropylamine

HRID 1504295Notes

Reaction equation

HRID 1504295 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].[OH-].[Na+]>O1CCCC1>[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

5

Reactant 3

HCID 8794PhenylacetonitrileHCID 14798Sodium HydroxideHCID 178418443HCID 178418443, compound

Product 1

HCID 1529231-Benzylcyclopropylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.5 g (38 mmol) of phenylacetonitrile was dissolved in 50 mL of tetrahydrofuran, mixed with 12.4 mL (41.9 mmol) of tetraisopropyl propylorthotitanate and 78 mL (76 mmol) of 0.98M ethylmagnesium bromide in tetrahydrofuran and stirred at room temperature for 1 hour. After the stirring, 9.6 mL (78 mmol) of boron trifluoride ethyl etherate complex was added, and the reaction solution was stirred at room temperature for another 1 hour. After completion of the reaction, 2 M aqueous sodium hydroxide was added, and the reaction solution was extracted with diethyl ether. After addition of 3 M hydrochloric acid, the organic layer was separated. The resulting aqueous layer was basified with 5 M aqueous sodium hydroxide and extracted with methylene chloride.

Workup

  1. additionAfter the stirring, 9.6 mL (78 mmol) of boron trifluoride ethyl etherate complex was added
  2. stirringthe reaction solution was stirred at room temperature for another 1 hour
  3. additionwas added
  4. extractionthe reaction solution was extracted with diethyl ether
  5. additionAfter addition of 3 M hydrochloric acid
  6. customthe organic layer was separated
  7. extractionextracted with methylene chloride

Sources & evidence

ORD record
ord-be2f89d01baa49cb8be2ea8d5d834e92
Source dataset
uspto-grants-2015_12
Patent number
US09212348B2

Reaction notes

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