Hydrochloric Acid → HCID 22414393, compound

HRID 486682Notes

Reaction equation

HRID 486682 reaction equation
[CH2:1]([NH:3][CH:4]([C:19]1[S:20][CH:21]=[CH:22][C:23]=1[CH3:24])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12]C(=O)C(C)(C)C)[CH3:2].[ClH:25]>>[ClH:25].[ClH:25].[NH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][CH:4]([C:19]1[S:20][CH:21]=[CH:22][C:23]=1[CH3:24])[NH:3][CH2:1][CH3:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 10315506HCID 10315506, compound

Product 1

HCID 22414393HCID 22414393, compound

Procedure

A solution of 9.2 g of N-[2-[2-(ethylamino)-2-(3-methyl-2-thienyl)ethyl]phenyl]-2,2-dimethylpropanamide in 160 ml of 6N hydrochloric acid was refluxed for 8 hrs. The solution was decanted over ice and basified with 50% sodium hydroxide solution. The aqueous mixture was extracted with dichloromethane, and the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by Preparative HPLC (Water Associates Prep LC/System 500 A, silica gel, eluted with methanol, flow rate of 200 ml/min, Gow-Mac Model 80-800 uv detector). The appropriate fractions were collected and concentrated. The residue was dissolved in ether, filtered, and concentrated. The residue was dissolved in methanol, ethereal-hydrogen chloride was added, and the solution was diluted with anhydrous ether to afford 5.0 g of product, mp 202°-204° C.

Workup

  1. customThe solution was decanted over ice and basified with 50% sodium hydroxide solution
  2. extractionThe aqueous mixture was extracted with dichloromethane
  3. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by Preparative HPLC (Water Associates Prep LC/System 500 A, silica gel, eluted with methanol, flow rate of 200 ml/min, Gow-Mac Model 80-800 uv detector)
  7. customThe appropriate fractions were collected
  8. concentrationconcentrated
  9. dissolutionThe residue was dissolved in ether
  10. filtrationfiltered
  11. concentrationconcentrated
  12. dissolutionThe residue was dissolved in methanol
  13. additionethereal-hydrogen chloride was added
  14. additionthe solution was diluted with anhydrous ether

Sources & evidence

ORD record
ord-4b229dc35f5a47409b87f13fd67f01ef
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Reaction notes

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