Isopropylamine → 4-[2-(1-Methylethyl)aminoethoxy]phenol

HRID 2417993Notes

Reaction equation

HRID 2417993 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[CH:12]([NH2:15])([CH3:14])[CH3:13]>>[CH3:13][CH:12]([NH:15][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH3:14]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 128339324-(2-Bromoethoxy)phenol

Product 1

HCID 133384854-[2-(1-Methylethyl)aminoethoxy]phenolYield 59%

Procedure

4-(2-Bromoethoxy)phenol (41 g) was added to 300 ml of isopropylamine and the solution was heated for 12 hours at 100° under nitrogen at 250 psi. Excess isopropylamine was removed in vacuo and 300 ml of water added to dissolve the residue. The solution was basified with solid potassium carbonate and the oil extracted with ether. The ether extract was dried over anhydrous potassium carbonate. After the solvent was removed in vacuo and the residue was crystallized from acetone-hexane to yield 21.8 g (59%) of 4-[2-(1-methylethyl)aminoethoxy]phenol, mp 78°-80°.

Workup

  1. temperaturethe solution was heated for 12 hours at 100° under nitrogen at 250 psi
  2. customExcess isopropylamine was removed in vacuo and 300 ml of water
  3. additionadded
  4. dissolutionto dissolve the residue
  5. extractionthe oil extracted with ether
  6. extractionThe ether extract
  7. dry with materialwas dried over anhydrous potassium carbonate
  8. customAfter the solvent was removed in vacuo
  9. customthe residue was crystallized from acetone-hexane

Sources & evidence

ORD record
ord-91f609c4cb2f401796d38ab1ca9a94f2
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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