Acetic Acid → N-benzyl-1-phenylethylamine

HRID 2416177Notes

Reaction equation

HRID 2416177 reaction equation
[CH2:1]([N:8]=[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(P(C1C=C(C)C=C(C)C=1)C1C=C(C)C=C(C)C=1)C.C(O)(=O)C.[H][H]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:1]([NH:8][CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 297338N-benzyl-1-phenylethanimineHCID 57230745HCID 57230745, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 519427N-benzyl-1-phenylethylamine

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Procedure

The process is carried out as in Example 6, but the reaction conditions are modified as follows: 0.636 g (3 mmol) of N-benzyl-N-(1-phenylethylidene)amine, 10.2 mg (0.0152 mmol) of [Ir(1,5-cyclooctadiene)Cl]2, 21.4 mg (0.0333 mmol) of {(R)-1-[(S)-2-diphenylphosphino)ferrocenyl]}ethyl-di(3,5-dimethylphenyl)phosphine (ligand) and 15 mg (0.04 mmol) of tetrabutylammonium iodide, 2 ml of acetic acid, 15 ml of toluene, 30 bar of hydrogen, reaction temperature: 25° C. The reaction time is 20 minutes. The conversion is complete, the ee 31%.

Workup

  1. customthe reaction conditions
  2. custom25° C

Sources & evidence

ORD record
ord-2ca8f37cc2294b07b0de46e71d579a36
Source dataset
uspto-grants-2004_11
Patent number
US06822118B1

Reaction notes

Loading…