Ammonia → 3-Phenoxy-3-phenyl-1-propanamine

HRID 1446794Notes

Reaction equation

HRID 1446794 reaction equation
[O:1]([CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:18]>C(O)C>[O:1]([CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][CH2:10][NH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 12851438(3-Chloro-1-phenoxypropyl)benzene

Product 1

HCID 128074853-Phenoxy-3-phenyl-1-propanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Eight grams of 3-phenoxy-3-phenylpropylchloride were heated with 150 ml. of liquid ammonia in a high pressure reactor at 100° C. for 20 hours. The volatile constituents of the reaction mixture were evaporated, and the residue, comprising 3-phenoxy-3-phenylpropylamine formed in the above reaction, was dissolved in ethanol and the volatile constituents again removed by evaporation. The resulting residue was dissolved in a mixture of ether and 5 N aqueous sodium hydroxide. The ether layer was separated, and the alkaline aqueous layer extracted three more times with ether. The ether extracts were combined, and the combined extracts washed with water. The combined ether extracts were in turn extracted twice with 2 N aqueous hydrochloric acid, the primary amine passing into the acidic layer. The acidic extracts were combined and made basic by the addition of an excess of 5 N aqueous sodium hydroxide. The primary amine, being insoluble in the basic layer, separated and was extracted into ether. The ether extract was separated, and the basic solution extracted twice more with ether. The ether extracts were combined, the combined extracts washed with saturated aqueous sodium chloride and then dried. Evaporation of the ether in vacuo yielded 3-phenoxy-3-phenylpropylamine as an oil. The oxalate salt of the primary amine was prepared and melted at 170°-173° C.

Workup

  1. customThe volatile constituents of the reaction mixture were evaporated
  2. customformed in the above reaction
  3. customthe volatile constituents again removed by evaporation
  4. dissolutionThe resulting residue was dissolved in a mixture of ether and 5 N aqueous sodium hydroxide
  5. customThe ether layer was separated
  6. extractionthe alkaline aqueous layer extracted three more times with ether
  7. washthe combined extracts washed with water
  8. extractionextracted twice with 2 N aqueous hydrochloric acid
  9. additionmade basic by the addition of an excess of 5 N aqueous sodium hydroxide
  10. customseparated
  11. extractionwas extracted into ether
  12. extractionThe ether extract
  13. customwas separated
  14. extractionthe basic solution extracted twice more with ether
  15. washthe combined extracts washed with saturated aqueous sodium chloride
  16. customdried
  17. customEvaporation of the ether in vacuo

Sources & evidence

ORD record
ord-822ee39f0164414aaed0fb4654231a23
Source dataset
uspto-grants-1982_02
Patent number
US04313896

Reaction notes

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