Isopropylamine → α-[[(1-Methylethyl)amino]methyl]benzenemethanol

HRID 1758251Notes

Reaction equation

HRID 1758251 reaction equation
[CH2:1]1[O:9][CH:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:10]([NH2:13])([CH3:12])[CH3:11]>CO>[CH:10]([NH:13][CH2:1][CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[OH:9])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 7276Styrene Oxide

Product 1

HCID 20119α-[[(1-Methylethyl)amino]methyl]benzenemethanolYield 49.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 120 g (1 mole) styrene oxide and 59 g (1 mole) of isopropylamine are heated under reflux for 5 hours in 400 ml of methanol. The mixture is dry evaporated and the residue is dissolved in 500 ml of water. The desired free base which has precipitated is filtered and the solution is washed with 100 ml of hexane. The base is recrystallized from hexane, and the crystals are filtered and washed with 50 ml hexane and then dried. 89 g (yield=49%) of 2-isopropylamino-1-phenyl-1-ethanol are obtained. M.P. 90° C.

Workup

  1. temperatureare heated
  2. customThe mixture is dry
  3. customevaporated
  4. dissolutionthe residue is dissolved in 500 ml of water
  5. customThe desired free base which has precipitated
  6. filtrationis filtered
  7. washthe solution is washed with 100 ml of hexane
  8. customThe base is recrystallized from hexane
  9. filtrationthe crystals are filtered
  10. washwashed with 50 ml hexane
  11. customdried

Sources & evidence

ORD record
ord-cf2f3815528347f68dd9f42852b636c7
Source dataset
uspto-grants-1983_02
Patent number
US04372969

Reaction notes

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