HCID 178482133, compound → HCID 178482134, compound

HRID 504160Notes

Reaction equation

HRID 504160 reaction equation
C(OC(=O)[NH:10][C@@H:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)/[CH:12]=[N:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][CH3:21])C1C=CC=CC=1>C(O)C.[Pd]>[NH2:10][C@@H:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)/[CH:12]=[N:13]/[C:14]1[C:15]([NH:20][CH3:21])=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 178482133HCID 178482133, compound

Product 1

HCID 178482134HCID 178482134, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

{(S)-1-Benzyl-2-[(E)-2-methylamino-phenylimino]-ethyl}-carbamic acid benzyl ester (0.075 g, 0.20 mmol) was dissolved in absolute ethanol (7 mL) and treated with 10% palladium on carbon (0.040 g). The resulting suspension was shaken under 60-65 psi H2 at room temperature for 16 h. The suspension was filtered and the filter cake washed with MeOH (−100 mL), and the combined filtrates concentrated in vacuo to give N-[(S)-2-Amino-3-phenyl-prop-(E)-ylidene]-N′-methyl-benzene-1,2-diamine, as a light yellow oil (0.052 g, approximately quantitative yield): ES+ LC/MS m/e 238 (M+H), RT=3.12 min.

Workup

  1. filtrationThe suspension was filtered
  2. washthe filter cake washed with MeOH (−100 mL)
  3. concentrationthe combined filtrates concentrated in vacuo

Sources & evidence

ORD record
ord-ec08892d92cd4093a3130d013059bb36
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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