Piperazine → HCID 70607676, compound

HRID 1448145Notes

Reaction equation

HRID 1448145 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:8]1[CH:9]=[C:10]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[N+:12]([O-:14])[CH:13]=1>>[N:1]1([C:8]2[CH:9]=[C:10]([O:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:11]=[N+:12]([O-:14])[CH:13]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 70607181HCID 70607181, compound

Product 1

HCID 70607676HCID 70607676, compound

Conditions

Temperature
150 °C

Procedure

An intimate mixture of 43 g of piperazine with 26.6 g of 5-bromo-3-phenoxypyridine N-oxide [Agr. Biol. Chem., 34, 68 (1970)] is heated at 150° C. for five hours. The oil is concentrated at reduced pressure to remove excess piperazine. The mixture is dissolved in 1500 ml of dichloromethane, washed with excess 25% sodium hydroxide solution, dried over anhydrous MgSO4, filtered and concentrated to yield 5-piperazinyl-3-phenoxypyridine N-oxide as an oil. The oil is dissolved in 200 ml of toluene-methanol, (95-5) and chromatographed over 400 g, silica gel in toluene-methanol, (95-5). 5-Bromo-3-phenoxy-pyridine N-oxide is eluted first. Elution with toluene-methanol (50:50) yields 5-piperazinyl-3-phenoxypyridine N-oxide; mp 107°-115° C. after drying at 0.1 mm pressure for 16 hours.

Workup

  1. concentrationThe oil is concentrated at reduced pressure
  2. customto remove excess piperazine
  3. dissolutionThe mixture is dissolved in 1500 ml of dichloromethane
  4. washwashed with excess 25% sodium hydroxide solution
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f84687b7896547af9a9a82bb61c82db5
Source dataset
uspto-grants-1979_12
Patent number
US04179563

Reaction notes

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