Benzylamine → 245759-64-2

HRID 1420886Notes

Reaction equation

HRID 1420886 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[CH3:11])=[CH:5][CH:4]=1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H][H].[C:23]([OH:33])(=[O:32])[C@H:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:25]>[Pt].CO>[C:23]([OH:33])(=[O:32])[C@H:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:25].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([CH3:11])[NH:20][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 439616(S)-mandelic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 71721458245759-64-2

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

To 800 mL of methanol were added 328 g of 4-methoxyphenylacetone (2 mol) and 214 g of N-benzylamine (2 mol). The imine formation was exothermic and the solution warmed to 45° C. After reaction was complete, the solution was hydrogenated at 50 psi for 6-8 hours in the presence of 3.3 g of 5% platinum on carbon catalyst. When the hydrogen uptake had stopped, the reaction was filtered through diatomaceous earth, and the filter cake was washed with 200 mL of methanol. The combined filtrates were placed in a 6-liter flask and diluted with 4.2 liters of methanol. (S)-L-Mandelic acid (304 g, 2 mol) was added and the mixture heated with stirring to reflux to obtain a clear solution. The solution was cooled to room temperature, stirred at room temperature for two hours and the mandelic acid salt filtered off. The recrystallization was repeated three times to obtain 60-70 g of the mandelic acid salt of the benzyl amine having an isomeric purity greater than 99.8% and a melting point of 164° C.

Workup

  1. customAfter reaction
  2. filtrationthe reaction was filtered through diatomaceous earth
  3. washthe filter cake was washed with 200 mL of methanol
  4. customThe combined filtrates were placed in a 6-liter flask
  5. additiondiluted with 4.2 liters of methanol
  6. temperaturethe mixture heated
  7. temperatureto reflux
  8. customto obtain a clear solution
  9. temperatureThe solution was cooled to room temperature
  10. stirringstirred at room temperature for two hours
  11. filtrationthe mandelic acid salt filtered off
  12. customThe recrystallization

Sources & evidence

ORD record
ord-9de6cc5a25f145c8b478465498baa706
Source dataset
uspto-grants-2000_06
Patent number
US06071971

Reaction notes

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