Hydrochloric Acid → HCID 19784504, compound

HRID 2081825Notes

Reaction equation

HRID 2081825 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:22][CH3:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH3:21])=O.[ClH:26].[OH-].[Na+]>>[ClH:26].[ClH:26].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH:13]([NH:22][CH3:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH3:21]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15085942HCID 15085942, compound

Product 1

HCID 19784504HCID 19784504, compound

Procedure

A solution of 14.0 g of 2,2-dimethyl-N-[2-[2-methylamino-2-(2-ethylphenyl)ethyl]phenyl]propanamide and 100 ml of 6N hydrochloric acid was refluxed for 8 hr, cooled and poured into 250 ml of ice. The mixture was basified with 50% sodium hydroxide solution and extracted with dichloromethane. The extracts were combined, dried over anhydrous sodium sulfate and concentrated. The oil was dissolved in 50 ml methanol and the solution was treated with ethereal hydrogen chloride and diluted with 700 ml anhydrous ether. The solid was recrystallized from methanol/ether to give 2-amino-α-(2-ethylphenyl)-N-methylphenethylamine dihydrochloride, mp 251°-253° C. (dec).

Workup

  1. temperaturecooled
  2. extractionextracted with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. dissolutionThe oil was dissolved in 50 ml methanol
  6. additionthe solution was treated with ethereal hydrogen chloride
  7. additiondiluted with 700 ml anhydrous ether
  8. customThe solid was recrystallized from methanol/ether

Sources & evidence

ORD record
ord-917c20a9ed4e45d7919073c2e3ed89ca
Source dataset
uspto-grants-1993_02
Patent number
US05185465

Reaction notes

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