Water → HCID 15008258, compound

HRID 345770Notes

Reaction equation

HRID 345770 reaction equation
[C:1]1([CH2:7][NH:8][CH:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][C:16]=2[NH:17]C(=O)C(C)(C)C)[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O>C(O)CC.[OH-].[Na+]>[NH2:17][C:16]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[CH:9]([CH3:10])[NH:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 962WaterHCID 15008256HCID 15008256, compound

Product 1

HCID 15008258HCID 15008258, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of N-[3-[1-(phenylmethylamino)ethyl]-4-pyridinyl]-2,2-dimethylpropanamide (12.2 g) in 200 ml n-propanol and 25 ml 10% aqueous sodium hydroxide was stirred at reflux for sixteen hours and thereafter cooled, stirred with water and extracted with ethyl acetate/ether. The organic extract was washed with water and saturated sodium chloride solution and thereafter dried (anhydrous magnesium sulfate), filtered and concentrated to 8.7 g oil. This oil was eluted with 20% methanol in dichloromethane through silica via flash column chromatography to yield 8 g oil. This oil was eluted with 10% methanol in dichloromethane through silica via HPLC to yield 7 g oil. Following unseccessful attempts to purify this oil as salts, the reconverted free base was again eluted with 20% methanol in dichloromethane through silica via HPLC to yield 5.5 g oil. A 3.5 g portion was converted to the dimaleate salt in methanol/ether to yield 4.5 g solid, d 78°-80°. This salt was reconverted to the free base to afford a solid which was recrystallized from 50% ether/hexane to yield 1.9 g crystals, m.p. 107°-109°.

Workup

  1. temperatureat reflux for sixteen hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate/ether
  4. extractionThe organic extract
  5. washwas washed with water and saturated sodium chloride solution
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated to 8.7 g oil
  9. washThis oil was eluted with 20% methanol in dichloromethane through silica via flash column chromatography

Sources & evidence

ORD record
ord-61eca0f6316d4b7aa3bb77c27006dbb2
Source dataset
uspto-grants-1991_10
Patent number
US05059602

Reaction notes

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