Hydrochloric Acid → HCID 12915166, compound

HRID 257098Notes

Reaction equation

HRID 257098 reaction equation
[ClH:1].[CH2:2]([NH:4][CH:5]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)[CH3:3].C(O)C.[OH-].[K+].Cl>CCOCC>[ClH:1].[ClH:1].[NH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][CH:5]([NH:4][CH2:2][CH3:3])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 12915156HCID 12915156, compound

Product 1

HCID 12915166HCID 12915166, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.00 g of N-Ethyl-2-nitro-α-phenylphenethylamine hydrochloride is treated with 100 ml of hot 95% ethanol containing 1.10 g of potassium hydroxide for 15 minutes, after which the mixture is filtered and placed in a Paar flask. 0.15 g of 10% palladium on charcoal is added and the mixture is hydrogenated at room temperature and 50 psia for 3 hours, after which the catalyst is removed. The ethanol is evaporated from the filtrate and the resulting yellow oil is poured onto 100 ml of water. The biphasic aqueous mixture is extracted with methylene chloride (2×100 ml). The combined methylene chloride extracts are dried over anhydrous magnesium sulfate and the methylene chloride evaporated to afford a colorless oil. The oil is dissolved in 50 ml of ether. Ethereal hydrogen chloride (100 ml) is added precipitating the hydrochloride acid salt as an oil. The ethanol is evaporated and the oil is dissolved in 20 ml of i-propanol with heating. Upon cooling, white crystals, mp >248° C. dec, fell from solution providing 2-amino-N-ethyl-α-phenylphenethylamine dihydrochloride.

Workup

  1. filtrationafter which the mixture is filtered
  2. addition0.15 g of 10% palladium on charcoal is added
  3. customis hydrogenated at room temperature
  4. customafter which the catalyst is removed
  5. customThe ethanol is evaporated from the filtrate
  6. additionthe resulting yellow oil is poured onto 100 ml of water
  7. extractionThe biphasic aqueous mixture is extracted with methylene chloride (2×100 ml)
  8. dry with materialThe combined methylene chloride extracts are dried over anhydrous magnesium sulfate
  9. customthe methylene chloride evaporated
  10. customto afford a colorless oil
  11. customprecipitating the hydrochloride acid salt as an oil
  12. customThe ethanol is evaporated
  13. dissolutionthe oil is dissolved in 20 ml of i-propanol
  14. temperaturewith heating
  15. temperatureUpon cooling

Sources & evidence

ORD record
ord-c0f37099d37e4c0e8b225eebc8b020e9
Source dataset
uspto-grants-1993_11
Patent number
US05260339

Reaction notes

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