Isopropylamine → HCID 20341523, compound

HRID 1395052Notes

Reaction equation

HRID 1395052 reaction equation
[O:1]1[CH2:22][CH:2]1[CH2:3][O:4][C:5]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=[O:8].[CH:23]([NH2:26])([CH3:25])[CH3:24]>CO>[CH3:21][C:16]1[C:6]([C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[O:8])=[C:5]([CH:19]=[C:18]([CH3:20])[CH:17]=1)[O:4][CH2:3][CH:2]([OH:1])[CH2:22][NH:26][CH:23]([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 20341515{2,4-Dimethyl-6-[(oxiran-2-yl)methoxy]phenyl}(4-methylphenyl)methanone

Product 1

HCID 20341523HCID 20341523, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(2,3-epoxypropoxy)-4,4',6-trimethylbenzophenone (10.0 g.), isopropylamine (10 ml.) and anhydrous methanol (50 ml.) was heated at reflux for 17 hours. The solution was then evaporated in vacuo, and the residue was dissolved in water (100 ml.) containing concentrated hydrochloric acid (10 ml.). The solution was adjusted to a pH between 6 and 7 and was shaken with ethyl acetate. The aqueous phase was then adjusted to pH 12 by the addition of aqueous sodium hydroxide solution. The precipitated oil was extracted with ethyl acetate and the extract was washed with water, dried over anhydrous sodium sulphate and evaporated. The residue was dissolved in a hot mixture of light petroleum (b.p. 40°-60° C.; 75 ml.) and cyclohexane (3 ml.) and allowed to cool slowly. The solid was filtered off and recrystallized from cyclohexane (25 ml.) to give DL-1-(3,5-dimethyl-2-p-toluoylphenoxy)-2-hydroxy-3-isopropylaminopropane (5.9 g.), m.p. 89°-91° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 17 hours
  3. customThe solution was then evaporated in vacuo
  4. dissolutionthe residue was dissolved in water (100 ml.)
  5. additioncontaining concentrated hydrochloric acid (10 ml.)
  6. additionThe aqueous phase was then adjusted to pH 12 by the addition of aqueous sodium hydroxide solution
  7. extractionThe precipitated oil was extracted with ethyl acetate
  8. washthe extract was washed with water
  9. dry with materialdried over anhydrous sodium sulphate
  10. customevaporated
  11. dissolutionThe residue was dissolved in a hot mixture of light petroleum (b.p. 40°-60° C.; 75 ml.) and cyclohexane (3 ml.)
  12. temperatureto cool slowly
  13. filtrationThe solid was filtered off
  14. customrecrystallized from cyclohexane (25 ml.)

Sources & evidence

ORD record
ord-9d4cedad701343fdb4f2468b8e864969
Source dataset
uspto-grants-1980_05
Patent number
US04201790

Reaction notes

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