Isopropylamine → HCID 20341530, compound

HRID 1395055Notes

Reaction equation

HRID 1395055 reaction equation
[O:1]1[CH2:22][CH:2]1[CH2:3][O:4][C:5]1[C:18]([CH3:19])=[C:17]([CH3:20])[CH:16]=[C:15]([CH3:21])[C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].[CH:23]([NH2:26])([CH3:25])[CH3:24]>CO>[C:7]([C:6]1[C:15]([CH3:21])=[CH:16][C:17]([CH3:20])=[C:18]([CH3:19])[C:5]=1[O:4][CH2:3][CH:2]([OH:1])[CH2:22][NH:26][CH:23]([CH3:25])[CH3:24])(=[O:8])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 20341519Phenyl{3,4,6-trimethyl-2-[(oxiran-2-yl)methoxy]phenyl}methanone

Product 1

HCID 20341530HCID 20341530, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(2,3-epoxypropoxy)-3,4,6-trimethylbenzophenone (10.0 g.), isopropylamine (10 ml.) and anhydrous methanol (100 ml.) was heated at reflux for 17 hours. The solution was evaporated in vacuo and the residue was dissolved in water (100 ml.) containing concentrated hydrochloric acid (6 ml.). The solution was filtered through charcoal and kieselguhr, adjusted to pH 11 by means of 2 N aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed 3 times with water, dried over anhydrous sodium sulphate and evaporated. The residue was recystallized from cyclohexane to give DL-1-(2-benzoyl-3,5,6-trimethylphenoxy)-2-hydroxy-3-isopropylaminopropane (6.6 g.), m.p. 121°-123° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 17 hours
  3. customThe solution was evaporated in vacuo
  4. dissolutionthe residue was dissolved in water (100 ml.)
  5. additioncontaining concentrated hydrochloric acid (6 ml.)
  6. filtrationThe solution was filtered through charcoal and kieselguhr
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed 3 times with water
  9. dry with materialdried over anhydrous sodium sulphate
  10. customevaporated

Sources & evidence

ORD record
ord-cecc382f4a0842e58585e8a1db061759
Source dataset
uspto-grants-1980_05
Patent number
US04201790

Reaction notes

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