4-Benzylideneaminopyridine → N-([alpha-phenyl]-n-pentyl)-4-pyridinamine

HRID 1448605Notes

Reaction equation

HRID 1448605 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH:6](=[N:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCCCCC.CCOCC>[C:7]1([CH:6]([NH:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH2:1][CH2:2][CH2:3][CH3:4])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 6428664-BenzylideneaminopyridineHCID 178418339Butyllithium

Product 1

HCID 23458002N-([alpha-phenyl]-n-pentyl)-4-pyridinamineYield 32.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

0.03 Mole of butyl lithium in hexane as a 15% w/w solution was added dropwise to a stirred, cooled (-10° C.) solution of 5.46 grams (0.03 mole) of 4-benzylideneamino pyridine in 10 milliliters of dry ether. The mixture was allowed to warm to room temperature and then poured onto ice and extracted with methylene chloride. The organic phase was separated and extracted with 2 N hydrochloric acid. The extracts were basified with 2 N sodium hydroxide and extracted into methylene chloride. The resulting methylene chloride solution was dried (MgSO4) and decolourised with charcoal. The solvent was removed and the resulting light oil (5.75 grams) was crystallised and recrystallised from a toluene/petrol (60°-80° C.) mixture affording 2.36 grams of N-([α-phenyl]-n-pentyl)-4-pyridinamine, melting point 118°-8.5°.

Workup

  1. additionpoured onto ice
  2. extractionextracted with methylene chloride
  3. customThe organic phase was separated
  4. extractionextracted with 2 N hydrochloric acid
  5. extractionextracted into methylene chloride
  6. dry with materialThe resulting methylene chloride solution was dried (MgSO4)
  7. customThe solvent was removed
  8. customthe resulting light oil (5.75 grams) was crystallised
  9. customrecrystallised from a toluene/petrol (60°-80° C.) mixture

Sources & evidence

ORD record
ord-91f7e22f425d409986ed2ad166e33fde
Source dataset
uspto-grants-1979_12
Patent number
US04180670

Reaction notes

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