Reaction #452479

ord-44c7f45ad7ea43e1a71cb8c15e4f41e7

Reaction equation

COc1ccccc1N1CCN(CCCN)CC1
product
COc1ccccc1N1CCN(CCCN)CC1
4-(2-Methoxyphenyl)-1-(3-aminopropyl)piperazine
Clc1ccccn1
2-chloropyridine
COc1ccccc1N1CCN(CCCNc2ccccn2)CC1
product
Yield 13.4%
COc1ccccc1N1CCN(CCCNc2ccccn2)CC1
4-(2-Methoxyphenyl)-1-(3-(pyridin-2-yl)aminopropyl)piperazine
Yield 13.4%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureAfter cooling
  2. 2
    Washwashed with aqueous NaOH (3×50 ml)
  3. 3
    Dryingdried (MgSO4)
  4. 4
    Otherevaporated in vacuo
  5. 5
    OtherThe residue was purified by chromatography [alumina; ethyl acetate-toluene (1:4)]

Procedure

The product of Example 27 (3.9 g, 16 mmol) and 2-chloropyridine (1.82 g, 16 mmol) were heated at 160° C. in a sealed vessel for 6 h. After cooling, the residue was taken up into CH2Cl2 (50 ml) washed with aqueous NaOH (3×50 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by chromatography [alumina; ethyl acetate-toluene (1:4)] to give the product (0.7 g) as a brown oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06127357uspto-grants-2000_10