Aniline → (-)-1-(1-Phenyl-2-propenyl)phenylamine

HRID 14439Notes

Reaction equation

HRID 14439 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O[CH2:12][CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)OC>>[C:15]1([CH:14]([C:2]2([NH2:1])[CH:7]=[CH:6][CH:5]=[CH:4][CH2:3]2)[CH:13]=[CH2:12])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 54135828Methyl 3-phenylprop-2-en-1-yl carbonate

Product 1

HCID 68584977(-)-1-(1-Phenyl-2-propenyl)phenylamine

Procedure

By the procedure with [(COD)IrCl]2 (6.7 mg, 0.010 mmol) and L1 (Sa,Sc,Sc) (10.8 mg, 0.020 mmol) the reaction of aniline (130 mg, 1.40 mmol) and methyl cinnamyl carbonate (188 mg, 0.980 mmol) was conducted at room temperature for 24 h. 1H NMR and GC analysis of the crude reaction mixture showed that the conversion of the reaction was less than 1%.

Workup

  1. custom1H NMR and GC analysis of the crude reaction mixture

Sources & evidence

ORD record
ord-2100cafdb4bd4016aca38deed8f67b56
Source dataset
uspto-grants-2010_06
Patent number
US07732365B2

Reaction notes

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