Hydrochloric Acid → 2-Amino-N-methyl-alpha-(3-methyl-2-thienyl)-5-trifluoromethylbenzeneethanamine dihydrochloride

HRID 486688Notes

Reaction equation

HRID 486688 reaction equation
CC(C)(C)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1[CH2:16][CH:17]([NH:24][CH3:25])[C:18]1[S:19][CH:20]=[CH:21][C:22]=1[CH3:23])=O.[ClH:28]>>[ClH:28].[ClH:28].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:8][C:7]=1[CH2:16][CH:17]([C:18]1[S:19][CH:20]=[CH:21][C:22]=1[CH3:23])[NH:24][CH3:25]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 19096191HCID 19096191, compound

Product 1

HCID 224144962-Amino-N-methyl-alpha-(3-methyl-2-thienyl)-5-trifluoromethylbenzeneethanamine dihydrochloride

Procedure

A solution of 8.29 g of 2,2-dimethyl-N-[2-[2-methylamino-2-(3-methyl-2-thienyl)ethyl]-4-trifluoromethylphenyl]propanamide and 250 ml of 6N hydrochloric acid was refluxed for 10 hr, with stirring. The cooled solution was decanted over crushed ice and water, basified with 50% sodium hydroxide solution, and extracted with dichloromethane. The combined organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was separated by preparative HPLC (Waters Associates Prep LC/System 500, silica gel, sample applied in and eluted with methanol, 200 ml/min flow rate). The appropriate fractions were combined and evaporated. The residue was dissolved in ether and allowed to stand for 1 hr. The solution was filtered and the filtrate concentrated. The residue crystallized during refrigerated storage. A solution of the residue and ~5 ml methanol was treated with excess ethereal hydrogen chloride, and the solution was gradually diluted with ether. The precipitate was collected, washed with ether, and dried in vacuo at 40° C. over sodium hydroxide pellets to give 0.29 g of product, mp 209°-212° C. (dec.).

Workup

  1. customThe cooled solution was decanted
  2. customover crushed ice and water
  3. extractionextracted with dichloromethane
  4. washThe combined organic phase was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was separated by preparative HPLC (Waters Associates Prep LC/System 500, silica gel, sample applied in and eluted with methanol, 200 ml/min flow rate)
  9. customevaporated
  10. dissolutionThe residue was dissolved in ether
  11. filtrationThe solution was filtered
  12. concentrationthe filtrate concentrated
  13. customThe residue crystallized during refrigerated storage
  14. additionA solution of the residue and ~5 ml methanol was treated with excess ethereal hydrogen chloride
  15. additionthe solution was gradually diluted with ether
  16. customThe precipitate was collected
  17. washwashed with ether
  18. dry with materialdried in vacuo at 40° C. over sodium hydroxide pellets

Sources & evidence

ORD record
ord-e09f6f31657849bfaf4e1d8e0c30c0d7
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Reaction notes

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