HCID 57857600, compound → 2-Bicyclopropyl-2-yl-phenylamine

HRID 17024Notes

Reaction equation

HRID 17024 reaction equation
C([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]1[CH2:17][CH:16]1[CH:18]1[CH2:20][CH2:19]1)C1C=CC=CC=1>O1CCCC1.[Pd]>[CH:16]1([CH:18]2[CH2:20][CH2:19]2)[CH2:17][CH:15]1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH2:8]

Participants

4

Reactant 1

HCID 57857600HCID 57857600, compound

Product 1

HCID 167270602-Bicyclopropyl-2-yl-phenylamineYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1 g of benzyl(2-bicyclopropyl-2-yl-phenyl)amine (3.8 mmol, trans/cis ratio of about 3:1) is dissolved in 15 ml of absolute tetrahydrofuran. Then 50 mg of Pd (5%) on activated carbon are added. Hydrogenation is then carried out, with stirring, for 1 hour at room temperature. After completion of the reaction, the catalyst is filtered off and the solvent is removed using a water jet vacuum. The product is purified by chromatography on silica gel (eluant:ethyl acetate/hexane 1/15). 0.61 g of 2-bicyclopropyl-2-ylphenylamine (92% of theory) is obtained in the form of a brownish liquid (trans/cis ratio of about 3:1).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst is filtered off
  3. customthe solvent is removed
  4. customThe product is purified by chromatography on silica gel (eluant:ethyl acetate/hexane 1/15)

Sources & evidence

ORD record
ord-94bc49a6260f4493b18197ad5ae865bc
Source dataset
uspto-grants-2010_06
Patent number
US07737301B2

Reaction notes

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