3-(N-Methyl-N-phenylamino)-2-hydroxypropylazide → 1-Amino-3-[methyl(phenyl)amino]propan-2-ol

HRID 2294353Notes

Reaction equation

HRID 2294353 reaction equation
[H][H].[CH3:3][N:4]([CH2:11][CH:12]([OH:17])[CH2:13][N:14]=[N+]=[N-])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>[Pd].C(O)C>[CH3:3][N:4]([CH2:11][CH:12]([OH:17])[CH2:13][NH2:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 214747453-(N-Methyl-N-phenylamino)-2-hydroxypropylazideHCID 178418361HCID 178418361, compound

Product 1

HCID 2725791-Amino-3-[methyl(phenyl)amino]propan-2-olYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogen was introduced into a mixture of 1.85 g of 3-(N-methyl-N-phenylamino)-2-hydroxypropylazide (prepared as described in Preparation 89), 0.9 g of 10% w/w palladium-on-carbon and 30 ml of ethanol for 1.5 hours. At the end of this time, the atmosphere was replaced with nitrogen, the palladium-on-carbon catalyst was removed from the reaction mixture by filtration, and the filtrate was concentrated by evaporation under reduced pressure, to give 1.6 g of the title compound which decomposed at 136° C.

Workup

  1. customthe palladium-on-carbon catalyst was removed from the reaction mixture by filtration
  2. concentrationthe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-bfb15e45eede44f7b725a4ae74b151d1
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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