2-Chloropyridine → N-{2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl}pyridin-2-amine

HRID 1603680Notes

Reaction equation

HRID 1603680 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH2:6][CH2:5]1.Cl[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>C(Cl)(Cl)Cl>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[NH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 79772-ChloropyridineHCID 103991861-(2-Aminoethyl)-4-(2-methoxyphenyl)piperazine

Product 1

HCID 10018417N-{2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl}pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

23.5 g of 1-(2-aminoethyl)-4-(2-methoxyphenyl)piperazine [Hexachemie-Reuil Malmaison-France] and 4.85 mL of 2-chloropyridine were stirred at 160° C. in a closed reaction vessel for 10.5 hours. The reaction mixture was cooled to room temperature, dissolved in 320 mL of chloroform and washed with 1N sodium hydroxide (3×320 mL), followed by water (2×400 mL). The organic layer was dried (sodium sulfate) and evaporated to dryness under reduced pressure. The crude product was purified by column flash chromatography eluting with an ethyl acetate-3N NH3 in methanol 100:2 mixture affording, after evaporation of the collected fractions, 5 g of the title compound as an oil. A sample was crystallized from ethyl acetate to give a solid melting at 89-94° C.

Workup

  1. washwashed with 1N sodium hydroxide (3×320 mL)
  2. dry with materialThe organic layer was dried (sodium sulfate)
  3. customevaporated to dryness under reduced pressure
  4. customThe crude product was purified by column flash chromatography
  5. washeluting with an ethyl acetate-3N NH3 in methanol 100:2 mixture
  6. customaffording
  7. customafter evaporation of the collected fractions, 5 g of the title compound as an oil
  8. customA sample was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-e4231e977d3e45559bfd0b17f08e5339
Source dataset
uspto-grants-1999_11
Patent number
US05990114

Reaction notes

Loading…