N,1-diphenylethan-1-imine → N-(1-Phenylethyl)aniline

HRID 546328Notes

Reaction equation

HRID 546328 reaction equation
CC(C)([O-])C.[K+].[C:7]1([C:13](=[N:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)(C)C.[Ru+2]>[C:16]1([NH:15][CH:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:14])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 555698N,1-diphenylethan-1-imineHCID 23665647Potassium tert-butoxide

Product 1

HCID 418090N-(1-Phenylethyl)aniline

Reagents, catalysts & solvents 2

HCID 3792939Ruthenium(2+)CatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

The reaction was carried out in a multiwell hydrogenation vessel. Dichloro-{1,2-Bis[(2R,5R)-2,5-diphenylphospholano]methane}[(1S,2S)-1,2-diphenylethylenediamine)] ruthenium (II) (2.2 mg, 0.0025 mmol) was suspended in degassed isopropanol (2 ml) in a Schlenk flask under nitrogen. Added potassium tert-butoxide (1M in tert-butanol, 0.025 ml) and heated until a yellow solution was obtained. The glass liner was charged with N-(1-phenylethylidene)aniline (98 mg, 0.50 mmol). Charged to 10 bar nitrogen and vented (×5). Added the precatalyst solution and charged to 10 bar nitrogen and vented (×2). Commenced stirring at 1000 rpm and heated to 60° C. Charged to 10 bar H2 and stirred for 18 h. Cooled to room temperature, vented and evaporated to give phenyl-(1-phenylethyl)amine, conversion>99%, ee 71% (GC, sample derivatised by treatment with acetic anhydride pyridine, Chirasil DEX CB, 25 m×0.25 mm, injector/detector 200° C., helium 20 psi, 140° C. for 20 minutes then ramp at 5° C./min to 200° C., hold for 5 minutes, retention times 23.21 minutes and 23.45 minutes).

Workup

  1. customThe reaction was carried out in a multiwell hydrogenation vessel
  2. customwas obtained
  3. additionCharged to 10 bar nitrogen
  4. additionAdded the precatalyst solution
  5. additioncharged to 10 bar nitrogen
  6. additionCharged to 10 bar H2
  7. stirringstirred for 18 h
  8. temperatureCooled to room temperature
  9. customevaporated

Sources & evidence

ORD record
ord-80aaa4d56c394d5e8fde97f6d5b939a2
Source dataset
uspto-grants-2011_05
Patent number
US07935841B2

Reaction notes

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