Chloroform → HCID 21951121, compound

HRID 1770745Notes

Reaction equation

HRID 1770745 reaction equation
[NH2:1][C:2]([CH3:9])([CH3:8])[CH2:3][NH:4][CH2:5][CH2:6][OH:7].C(Cl)(Cl)Cl.[OH-:14].[Na+]>CC(C)=O>[OH:7][CH2:6][CH2:5][N:4]1[CH2:3][C:2]([CH3:9])([CH3:8])[NH:1][C:2]([CH3:9])([CH3:8])[C:3]1=[O:14]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 2268402-[(2-Amino-2-methylpropyl)amino]ethan-1-ol

Product 1

HCID 21951121HCID 21951121, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-((2-amino-2-methylpropyl)amino)ethanol (12 g, 91 mmol) in 90 mL of acetone was added chloroform (10.9 mL, 136 mmol) and the solution was cooled to 0° C. with an external ice bath. A solution of NaOH (50% by weight, 43.6 g, 545 mmol) was added slowly to the cold solution over several minutes and the resultant solution was stirred at 0° C. for 2 hours then allowed to warm to room temperature and stirred for an additional 18 hr. The crude reaction mixture was filtered to remove solids, washing with acetone, and the solution was concentrated to 20 g of a clear oil. A portion of the crude material was purified by a bulb-to-bulb distillation under reduced pressure to give 1.45 g of a clear oil, which was used directly in the next step without further purification. LRMS (ESI/APCI) m/z 201 [M+H]+.

Workup

  1. temperatureto warm to room temperature
  2. customThe crude reaction mixture
  3. filtrationwas filtered
  4. customto remove solids
  5. washwashing with acetone
  6. concentrationthe solution was concentrated to 20 g of a clear oil
  7. distillationA portion of the crude material was purified by a bulb-to-bulb distillation under reduced pressure

Sources & evidence

ORD record
ord-b8d9a6540c524b14afa817581abc9633
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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