Hydrazine hydrate (1:1) → 4-Hydrazinyl-6-(piperidin-1-yl)pyrimidine

HRID 37890Notes

Reaction equation

HRID 37890 reaction equation
O.[NH2:2][NH2:3].Cl[C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[N:8]=[CH:7][N:6]=1>C(O)C>[NH:2]([C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[N:8]=[CH:7][N:6]=1)[NH2:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5978704-Chloro-6-piperidin-1-ylpyrimidine

Product 1

HCID 441403054-Hydrazinyl-6-(piperidin-1-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

With stirring and at RT, 17.7 ml (18.2 g, 364.2 mmol) of hydrazine hydrate are added dropwise to a solution of 6.0 g (30.4 mmol) of 4-chloro-6-piperidin-1-ylpyrimidine in 50 ml of ethanol. The reaction solution is stirred at 80° C. for a further 16 h. For work-up, the mixture is concentrated under reduced pressure, the residue is stirred in water, the precipitated solid is filtered off, the filter residue is washed twice with in each case 150 ml of water and twice with in each case 100 ml of diethyl ether and the product is dried under reduced pressure.

Workup

  1. stirringThe reaction solution is stirred at 80° C. for a further 16 h
  2. concentrationFor work-up, the mixture is concentrated under reduced pressure
  3. stirringthe residue is stirred in water
  4. filtrationthe precipitated solid is filtered off
  5. washthe filter residue is washed twice with in each case 150 ml of water and twice with in each case 100 ml of diethyl ether
  6. customthe product is dried under reduced pressure

Sources & evidence

ORD record
ord-64a84a97abe3476381b6b4865a6319a0
Source dataset
uspto-grants-2013_09
Patent number
US08524699B2

Reaction notes

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