Hydrochloric Acid → 2-Phenylpropylamine hydrochloride

HRID 420823

Reaction equation

HRID 420823 reaction equation
C(O)C.[C:4]1([CH:10]([CH3:13])[C:11]#[N:12])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[ClH:14].[H][H]>C(OC)(C)(C)C>[ClH:14].[C:4]1([CH:10]([CH3:13])[CH2:11][NH2:12])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 157612-PhenylpropionitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 893322-Phenylpropylamine hydrochlorideYield 76.2%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Charge to an autoclave hydrogenation apparatus under nitrogen water-wet 5% palladium on carbon (453 g), ethanol (6.36 L), 2-phenylpropionitrile (636 g, 4.85 moles) and finally concentrated (12M) hydrochloric acid (613 g, 5.6 mole). Stir the mixture rapidly and pressurize to 75 to 78 psi with hydrogen. Heat the mixture 50° C. to 64° C. for 3 hours. Depressurize and filter the reaction mixture to afford two lots of filtrate. Concentrate filtrates under reduced pressure to approximately 400 mL each. Add methyl tert-butyl ether (MTBE) (2.2 L each) to each lot. Stir the precipitate overnight. Filter and wash solids with fresh MTBE (100 mL) and dry overnight. Combine the lots to afford 2-phenyl-1-propylamine HCl (634.4 g, 76.2%) as a white powder.

Workup

  1. additionCharge to an autoclave hydrogenation apparatus under nitrogen water-wet 5% palladium on carbon (453 g)
  2. temperatureHeat the mixture 50° C. to 64° C. for 3 hours
  3. filtrationDepressurize and filter the reaction mixture
  4. customto afford two lots of filtrate
  5. stirringStir the precipitate overnight
  6. filtrationFilter
  7. washwash solids with fresh MTBE (100 mL)
  8. customdry overnight

Sources & evidence

ORD record
ord-dc753b3f3cf94d54bf0285b696229e54
Source dataset
uspto-grants-2012_01
Patent number
US08097652B2

Linked notes

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