Methanol → 2-(4-Methylpiperazin-1-yl)pyridin-4-amine

HRID 912097Notes

Reaction equation

HRID 912097 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](Cl)[CH:3]=1.CO.C(OCC)C.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:4]2[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][N:5]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 531671-MethylpiperazineHCID 844322-Chloropyridin-4-amine

Product 1

HCID 118391892-(4-Methylpiperazin-1-yl)pyridin-4-amineYield 18.6%

Conditions

Temperature
135 °C

Procedure

4-Amino-2-chloropyridine (180 mg, 1.4 mmol) was dissolved in 1-methylpiperazine (1 ml), followed by heating at 135° C. for 16 hours in a pressure vessel. After cooling to room temperature, methanol (2 ml) and diethyl ether (2 ml) were added, and the deposited precipitate was filtered off. The resulting solid was washed with cooled diethyl ether followed by drying, to obtain a colorless crystal powder (50 mg, 18.6% yield).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe deposited precipitate was filtered off
  3. washThe resulting solid was washed with cooled diethyl ether
  4. customby drying

Sources & evidence

ORD record
ord-732c4830fe794c21b676248c636ce619
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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