Isopropylamine → HCID 18368279, compound

HRID 379709Notes

Reaction equation

HRID 379709 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=2[O:23][CH3:24])(=O)=O)=CC=1.[CH:26]([NH2:29])([CH3:28])[CH3:27]>O1CCOCC1>[CH:26]([NH:29][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[O:23][CH3:24])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 18368347HCID 18368347, compound

Product 1

HCID 18368279HCID 18368279, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
73 °C

Procedure

2-(2-Methoxy-4-nitrophenoxy)ethyl p-toluenesulfonate (19.5 g) and 70% aqueous isopropylamine solution (15.7 g) were dissolved into dioxane (100 ml) and the mixture was stirred for 9 hours at 73° C. After being concentrated under vacuum, the reaction mixture was dissolved into 2N HCl (50 ml) and washed with ethyl acetate (50 ml) two times. Resulting aqueous layer was neutralized with 2N sodium hydroxide (50 ml) and then extracted with ethyl acetate (100 ml). The organic layer was dehydrated with anhydrous sodium sulfate and then concentrated under vacuum to almost dryness to obtain N-isopropyl-2-(2-methoxy-4-nitrophenoxy)ethylamine (9.29 g) as yellowish oil.

Workup

  1. concentrationAfter being concentrated under vacuum
  2. dissolutionthe reaction mixture was dissolved into 2N HCl (50 ml)
  3. washwashed with ethyl acetate (50 ml) two times
  4. extractionextracted with ethyl acetate (100 ml)
  5. concentrationconcentrated under vacuum to almost dryness

Sources & evidence

ORD record
ord-410905dab30e47a180f50b94db518269
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

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