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

HRID 242237Notes

Reaction equation

HRID 242237 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

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

Workup

  1. stirringThe reaction solution is subsequently stirred at 80° C. for 16 h
  2. concentrationthe mixture is concentrated in vacuo
  3. stirringthe residue is stirred in water
  4. customthe solid which has precipitated out
  5. filtrationis filtered off
  6. washthe residue on the filter is washed twice with 150 ml water each time
  7. dry with materialtwice with 100 ml diethyl ether each time and the product is dried in vacuo

Sources & evidence

ORD record
ord-f4cdb5e898ee41eca076db80d9bf79ab
Source dataset
uspto-grants-2014_02
Patent number
US08653111B2

Reaction notes

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