Potassium Hydroxide → N-(oxiran-2-ylmethyl)aniline

HRID 508232Notes

Reaction equation

HRID 508232 reaction equation
Cl[CH2:2][CH:3]([OH:12])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[K+]>O1CCOCC1.CCOC(C)=O>[O:12]1[CH2:2][CH:3]1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 36402541-Anilino-3-chloropropan-2-ol

Product 1

HCID 18522547N-(oxiran-2-ylmethyl)anilineYield 95%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product of Step 3 (185.7 mg, 1.0 mmol, 1 equiv) in 1,4-dioxane (3.3 mL) was added KOH powder (67.3 mg, 1.2 mmol, 1.2 equiv). The mixture was stirred at room temperature for 24 hours. The mixture was diluted with EtOAc and washed with 1M HCl and brine. The organic layer was dried with MgSO4 and concentrated to give crude product. It was further purified by silica gel chromatography using 20% EtOAc/Hex to afford 141.8 mg colorless oil as product, yield 95.0%.

Workup

  1. washwashed with 1M HCl and brine
  2. dry with materialThe organic layer was dried with MgSO4
  3. concentrationconcentrated
  4. customto give crude product
  5. customIt was further purified by silica gel chromatography

Sources & evidence

ORD record
ord-c6e0f4394fac4981baacb36d8a198c26
Source dataset
uspto-grants-2015_08
Patent number
US09095572B2

Reaction notes

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