Benzylamine → HCID 57857600, compound

HRID 17022Notes

Reaction equation

HRID 17022 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:10][CH:9]1[CH:11]1[CH2:13][CH2:12]1.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])(C)(C)C.[Na+].C(OCC)(=O)C>C(COC)OC>[CH2:14]([NH:21][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:10][CH:9]1[CH:11]1[CH2:13][CH2:12]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 23676156Sodium t-butoxideHCID 673713862-(2-Chlorophenyl)bicyclopropyl

Product 1

HCID 57857600HCID 57857600, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

3 g of 2-(2-chlorophenyl)bicyclopropyl (15.6 mmol, trans/cis ratio of about 2:1), 2.5 g of benzylamine (23.4 mmol), 2.4 g of sodium tert-butanolate (25 mmol), 35 mg of Pd(II) acetate (0.16 mmol) and 60 mg of R(−)-di-tert-butyl-[1-[(S)-2-(dicyclohexylphosphanyl)-ferrocenyl]ethyl]phosphine (0.11 mmol) are dissolved in 30 ml of dimethoxyethane. The reaction mixture is heated to the reflux temperature of the solvent and is stirred for 24 hours. After cooling, ethyl acetate is added and the organic phase is washed with water. The solvent is removed using a water jet vacuum and the residue is dried. The product is purified by column chromatography on silica gel (eluant:ethyl acetate/hexane 1:15). 3.58 g of benzyl(2-bicyclopropyl-2-yl-phenyl)amine (87% of theory) are obtained in the form of a brown oil (trans/cis ratio of about 2:1).

Workup

  1. temperatureThe reaction mixture is heated to the reflux temperature of the solvent
  2. temperatureAfter cooling
  3. washthe organic phase is washed with water
  4. customThe solvent is removed
  5. customthe residue is dried
  6. customThe product is purified by column chromatography on silica gel (eluant:ethyl acetate/hexane 1:15)

Sources & evidence

ORD record
ord-02745a7007724ba18c99b68f891541fd
Source dataset
uspto-grants-2010_06
Patent number
US07737301B2

Reaction notes

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