HCID 19096193, compound → HCID 22414363, compound

HRID 486664Notes

Reaction equation

HRID 486664 reaction equation
[CH3:1][NH:2][CH:3]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11]C(=O)C(C)(C)C>Cl>[NH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][CH:3]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[NH:2][CH3:1]

Participants

3

Reactant 1

HCID 19096193HCID 19096193, compound

Product 1

HCID 22414363HCID 22414363, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of 7.13 g of N-[2-[2-(methylamino)-2-(3-pyridinyl)ethyl]phenyl]-2,2-dimethylpropanamide in 90 ml of 6N hydrochloric acid was refluxed for 5.5 hours and then allowed to stand overnight at room temperature. The solution was decanted over crushed ice, diluted with water (200 ml) and basified with 50% sodium hydroxide solution. The mixture was extracted with dichloromethane (3×150 ml) and the combined, organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to an oil. The oil was purified by preparative HPLC (Water's Associates Prep LC/System 500 A, silica gel, sample applied in dichloromethane, eluted with 2% triethylamine in methanol). Concentration of the appropriate fractions yielded 4.69 g of 2-amino-N-methyl-α-(3-pyridinyl)benzeneethanamine as an oil.

Workup

  1. customThe solution was decanted
  2. customover crushed ice
  3. additiondiluted with water (200 ml)
  4. extractionThe mixture was extracted with dichloromethane (3×150 ml)
  5. dry with materialorganic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. customThe oil was purified by preparative HPLC (Water's Associates Prep LC/System 500 A, silica gel, sample applied in dichloromethane, eluted with 2% triethylamine in methanol)

Sources & evidence

ORD record
ord-7afddd1ab96a46eea86973d72db96335
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Reaction notes

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