Hydrochloric Acid → 2-amino-N-methyl-alpha-(2-methylphenyl)phenethylamine dihydrochloride

HRID 1073292Notes

Reaction equation

HRID 1073292 reaction equation
CC(C)(C)C([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH:13]([NH:21][CH3:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])=O.[ClH:25]>>[ClH:25].[ClH:25].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH:13]([NH:21][CH3:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 150859412,2-Dimethyl-N-[2-[2-methylamino-2-(2-methylphenyl)ethyl]phenyl]propanamide

Product 1

HCID 197844692-amino-N-methyl-alpha-(2-methylphenyl)phenethylamine dihydrochloride

Procedure

2,2-Dimethyl-N-[2-[2-methylamino-2-(2-methylphenyl)ethyl]phenyl]propanamide (12 g) was treated with 60 ml of 6N hydrochloric acid solution. After refluxing and stirring for 8 hr, the solution was decanted over 100 g of ice and basified with 25 ml of a 50% sodium hydroxide solution. The aqueous mixture was extracted with dichloromethane, and the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. Purification was accomplished by preparative HPLC (silica gel, eluted with methanol). The appropriate fractions were collected, combined and concentrated. The residue was dissolved in methanol, treated with ethereal hydrogen chloride and diluted with anhydrous ether to afford 2-amino-N-methyl-α-(2-methylphenyl)phenethylamine dihydrochloride, mp 242°-245° C.

Workup

  1. temperatureAfter refluxing
  2. customthe solution was decanted over 100 g of ice and basified with 25 ml of a 50% sodium hydroxide solution
  3. extractionThe aqueous mixture was extracted with dichloromethane
  4. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. washwas accomplished by preparative HPLC (silica gel, eluted with methanol)
  9. customThe appropriate fractions were collected
  10. concentrationconcentrated
  11. dissolutionThe residue was dissolved in methanol
  12. additiontreated with ethereal hydrogen chloride
  13. additiondiluted with anhydrous ether

Sources & evidence

ORD record
ord-df82a908dace476381a70e56be262c57
Source dataset
uspto-grants-1990_11
Patent number
US04968721

Reaction notes

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