Butylamine → N-Butylpyridin-4-amine

HRID 928270Notes

Reaction equation

HRID 928270 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:8]([NH2:12])[CH2:9][CH2:10][CH3:11]>O>[CH2:8]([NH:12][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 122884-Chloropyridine

Product 1

HCID 14322667N-Butylpyridin-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-chloropyridine (2.0 g, 17.6 mmol), 50% butylamine in water (30 mL) was heated at 150° C. in a sealed tube for 24 h. The reaction mixture was evaporated, partitioned between 0.1 N NaOH and CH2Cl2, dried (Na2SO4) and evaporated. Crystallization in ether/petroleum ether 4:1 afforded 2.4 g of the title product 113 as a white powder (LCMS analysis).

Workup

  1. customThe reaction mixture was evaporated
  2. custompartitioned between 0.1 N NaOH and CH2Cl2
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customCrystallization in ether/petroleum ether 4:1

Sources & evidence

ORD record
ord-5917ff51b54b4b5d833ec8ac28c2bf0e
Source dataset
uspto-grants-2016_03
Patent number
US09290502B2

Reaction notes

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