Potassium Hydroxide → 2-(3-(Prop-1-en-2-yl)phenyl)propan-2-amine

HRID 2274935Notes

Reaction equation

HRID 2274935 reaction equation
[N:1]([C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH3:15])=[CH2:14])[CH:8]=1)([CH3:6])[CH3:5])=C=O.[OH-].[K+]>CC(O)(C)C>[C:13]([C:9]1[CH:8]=[C:7]([C:4]([NH2:1])([CH3:6])[CH3:5])[CH:12]=[CH:11][CH:10]=1)([CH3:15])=[CH2:14]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 6041521-(1-Isocyanato-1-methylethyl)-3-(1-methylethenyl)benzene

Product 1

HCID 147165412-(3-(Prop-1-en-2-yl)phenyl)propan-2-amineYield 63%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 1-(1-isocyanato-1-methyl-ethyl)-3-isopropenyl-benzene (10 g, 50 mmol) in t-BuOH (1000 mL) was added KOH (40.0 g, 71.6 mmol). The mixture was stirred at reflux for 3 h. The resultant mixture was cooled down to room temperature, concentrated and dissolved in CH2Cl2. Solid residue was filtered off and the organic layer was adjusted to pH<7 using conc. HCl. The ammonium salt was extracted with water. The aqueous layer was made basic using an aqueous NaOH solution[5% w/w, 200 ml] and free based amine was then extracted with CH2Cl2. The organic layers were combined, dried over Na2SO4, filtered and concentrated under reduced pressure to give 1-(3-isopropenyl-phenyl)-1-methyl-ethylamine (3.3 g, 63%).

Workup

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated
  3. dissolutiondissolved in CH2Cl2
  4. filtrationSolid residue was filtered off
  5. extractionThe ammonium salt was extracted with water
  6. extractionwas then extracted with CH2Cl2
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5290d5bb6acd48ceb57a70c07258b064
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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