Hydrochloric Acid → (-)-alpha-Amino-propiophenone

HRID 2367397Notes

Reaction equation

HRID 2367397 reaction equation
[N:1]([CH:4]([CH3:13])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])=[N+]=[N-].[ClH:14]>[Pd].CO>[ClH:14].[NH2:1][CH:4]([CH3:13])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 108884342-Azido-1-phenyl-1-propanone

Product 2

HCID 313Hydrochloric AcidHCID 107786(-)-alpha-Amino-propiophenoneYield 126.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Palladium on carbon (1.069 g, 1.005 mmol) was added to the solution of 2-azido-1-phenyl-1-propanone (1.76 g, 10.05 mmol) and hydrochloric acid (6.69 mL, 80 mmol) in CH3OH (50 mL) under nitrogen, and the reaction mixture was stirred under hydrogen overnight at 25° C. The mixture was filtered, washing with CH2Cl2 (50 mL) and CH3OH (100 mL), and concentrated. Water (100 mL) was added, and the resulting mixture was lyophilized to yield an HCl salt of the title compound (1.9 g) as a brown solid. LC-MS (ES) m/z=150 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashing with CH2Cl2 (50 mL) and CH3OH (100 mL)
  3. concentrationconcentrated
  4. additionWater (100 mL) was added

Sources & evidence

ORD record
ord-9915e6ded12842a688c9f358bb920c8b
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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