HCID 21442569, compound → HCID 21442578, compound

HRID 328526Notes

Reaction equation

HRID 328526 reaction equation
[ClH:1].[CH3:2][C:3]([NH2:19])([CH3:18])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1>[Pt](=O)=O.CO>[ClH:1].[CH3:18][C:3]([NH2:19])([CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 21442569HCID 21442569, compound

Product 1

HCID 21442578HCID 21442578, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.45 gram of α,α-dimethyl-4-(phenylethynyl) -benzylamine hydrochloride, 61 ml. of absolute methanol, and 163 mg. of platinum dioxide catalyst is hydrogenated at 40 p.s.i. for one hour. The hydrogenation is stopped, the catalyst is removed by filtration, and the methanol is removed by evaporation. The residue is partitioned between benzene and 10% sodium hydroxide solution. The benzene phase is washed well with water, dried over magnesium sulfate, filtered, and the benzene is evaporated. The residual oil is dissolved in ether and treated with ethanolic hydrogen chloride. The precipitate is collected and recrystallized from isopropanol and ether to give α,α-dimethyl-4-phenethylbenzylamine hydrochloride, m.p. 225°-228° C.

Workup

  1. customthe catalyst is removed by filtration
  2. customthe methanol is removed by evaporation
  3. customThe residue is partitioned between benzene and 10% sodium hydroxide solution
  4. washThe benzene phase is washed well with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe benzene is evaporated
  8. dissolutionThe residual oil is dissolved in ether
  9. additiontreated with ethanolic hydrogen chloride
  10. customThe precipitate is collected
  11. customrecrystallized from isopropanol and ether

Sources & evidence

ORD record
ord-14e2ee66fd734a82a189e188585e983b
Source dataset
uspto-grants-1977_04
Patent number
US04017543

Reaction notes

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