HCID 21951129, compound → 2-[(2-Amino-2-methylpropyl)amino]ethan-1-ol

HRID 1770744Notes

Reaction equation

HRID 1770744 reaction equation
[CH3:1][C:2]([N+:9]([O-])=O)([CH3:8])[CH2:3][NH:4][CH2:5][CH2:6][OH:7]>CO.[Ni].O>[NH2:9][C:2]([CH3:8])([CH3:1])[CH2:3][NH:4][CH2:5][CH2:6][OH:7]

Participants

5

Reactant 1

HCID 21951129HCID 21951129, compound

Product 1

HCID 2268402-[(2-Amino-2-methylpropyl)amino]ethan-1-olYield 78%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-((2-methyl-2-nitropropyl)amino)ethanol (20.4 g, 126 mmol) in methanol (120 ml) was added a slurry of 50% Raney Nickel® in H2O (6 ml). The vessel was pressurized with H2 (450 psi) and the suspension stirred for 19 h. The mixture was filtered through Celite and concentrated in vacuo to give 20 g of a crude liquid, which was distilled under vacuum (<1 mbar, 100-125° C.) to give 13 g of a clear liquid, which was found to be partially purified and was used directly in the next step without purification. LRMS (ESI/APCI) m/z 133 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customto give 20 g of a crude liquid, which
  4. distillationwas distilled under vacuum (<1 mbar, 100-125° C.)

Sources & evidence

ORD record
ord-e79538a208514dc2bab55a69f72a986c
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

Loading…