Ammonia → HCID 70432000, compound

HRID 980192Notes

Reaction equation

HRID 980192 reaction equation
[CH2:1]([CH:7](C)[C:8]([NH2:17])([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)O)[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.F[C:20](F)(F)C(O)=O.N>C(Cl)CCl>[C:13]1([CH3:16])[CH:12]=[CH:11][C:10]([CH:8]2[C:7]3[CH:1]=[CH:2][O:6][C:5]=3[CH2:4][CH:3]([CH3:20])[NH:17]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 86741209HCID 86741209, compound

Product 1

HCID 70432000HCID 70432000, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Twenty grams (0.08 mol) of 2-furfuryl-2-methyl-amino-1-p-methyl-phenyl-ethanol were dissolved in 100 ml of ethylene chloride and heated to boiling point for three hours with 100 ml of trifluoroacetic acid. The reaction mixture was poured onto ice and neutralized with concentrated ammonia. The organic constituents were extracted with ether. Aftery drying, the ether was distilled off in vacuo. The residue was purified over silica gel [cyclohexane/ethyl acetate (1:1)]. After the solvent was distilled off in vacuo, the residue was dissolved in acetate. After addition of ethereal hydrochloric acid, the hydrochloride of the title compound crystallized out.

Workup

  1. temperatureheated
  2. customfor three hours
  3. extractionThe organic constituents were extracted with ether
  4. customAftery drying
  5. distillationthe ether was distilled off in vacuo
  6. customThe residue was purified over silica gel [cyclohexane/ethyl acetate (1:1)]
  7. distillationAfter the solvent was distilled off in vacuo
  8. dissolutionthe residue was dissolved in acetate
  9. additionAfter addition of ethereal hydrochloric acid
  10. customthe hydrochloride of the title compound crystallized out

Sources & evidence

ORD record
ord-35675be7f3a54de4ac7381660d6f4429
Source dataset
uspto-grants-1987_01
Patent number
US04636510

Reaction notes

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