Hydrochloric Acid → (4-Isopropylphenyl)[(2-methoxy-5-pyridyl)methyl]amine

HRID 218546Notes

Reaction equation

HRID 218546 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl.C(=O)([O-])O.[Na+]>C1COCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH2:11][C:13]2[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 17854296N-(4-isopropylphenyl)-6-methoxypyridine-3-carboxamide

Product 1

HCID 21957879(4-Isopropylphenyl)[(2-methoxy-5-pyridyl)methyl]amineYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A BH3-THF complex/1M THF solution (6.3 mL) was added to N-(4-isopropylphenyl)-6-methoxypyridine-3-carboxamide (0.76 g), and the mixture was heated under reflux for 4 hr. After cooling the reaction mixture, 1 mol/L hydrochloric acid (15 mL) was added and the mixture was stirred at room temperature for one day. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give (4-isopropylphenyl)[(6-methoxypyridin-3-yl)methyl]amine (0.62 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. additionwas added
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b39c0595e57c498e9e8019b97e0a0805
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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