Piperazine → 1-(3-Methoxypyridin-2-yl)piperazine

HRID 1031481Notes

Reaction equation

HRID 1031481 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:8]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][N:9]=1>>[CH3:15][O:14][C:13]1[C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 903642-Bromo-3-methoxypyridine

Product 1

HCID 127904951-(3-Methoxypyridin-2-yl)piperazineYield 82%

Procedure

Anhydrous piperazine (45.6 g) and 2-bromo-3-methoxypyridine (10.0 g) were heated neat in an autoclave at 100° C. for 20 h. Upon cooling, the mixture was treated with 5% NaCO3 (20 mL) and extracted with CH2Cl2 (3×50 mL). The extracts were dried using anhydrous K2CO3, filtered, and concentrated under reduced pressure to yield 1-(3-methoxy-2pyridinyl)piperazine (III; 8.43 g; 82%) after silica gel chromatography (CH2Cl2/MeOH/NH4OH; 93:7:0.7).

Workup

  1. temperatureUpon cooling
  2. extractionextracted with CH2Cl2 (3×50 mL)
  3. customThe extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ac22737b2ca4d35bb5b4bd5a4110501
Source dataset
uspto-grants-1990_09
Patent number
US04954502

Reaction notes

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