Benzylamine → HCID 57857600, compound

HRID 17023Notes

Reaction equation

HRID 17023 reaction equation
Br[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 167270592-(2-Bromophenyl)-1,1'-bi(cyclopropyl)HCID 23676156Sodium t-butoxide

Product 1

HCID 57857600HCID 57857600, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

3.7 g of 2-(2-bromophenyl)bicyclopropyl (15.6 mmol, trans/cis ratio of about 3:1), 2.0 g of benzylamine (18.7 mmol), 2.1 g of sodium tert-butanolate (21.8 mmol), 3.5 mg of Pd(II) acetate (0.016 mmol) and 8.6 mg of R(−)-di-tert-butyl-[1-[(S)-2-(dicyclohexylphosphanyl)-ferrocenyl]ethyl]phosphine (0.016 mmol) are dissolved in 30 ml of dimethoxyethane. The reaction mixture is heated to 70° C. and stirred for 24 hours. After cooling, ethyl acetate is added. 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). 3.47 g of benzyl(2-bicyclopropyl-2-yl-phenyl)amine (84% of theory) are obtained in the form of a brown oil (trans/cis ratio of about 3:1).

Workup

  1. temperatureAfter cooling
  2. washThe organic phase is washed with water
  3. customThe solvent is removed
  4. customthe residue is dried
  5. customThe product is purified by column chromatography on silica gel (eluant:ethyl acetate/hexane 1:15)

Sources & evidence

ORD record
ord-e083601a91f44099b2b9c26e1aae9027
Source dataset
uspto-grants-2010_06
Patent number
US07737301B2

Reaction notes

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