Piperazine → HCID 47002240, compound

HRID 717806Notes

Reaction equation

HRID 717806 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C(O)CCC>[ClH:1].[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 2598065-Chloro-2-nitropyridine

Product 1

HCID 47002240HCID 47002240, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
95 °C

Procedure

A nitrogen-flushed, suitably equipped 22 L 4-neck round bottom flask is charged with 1392 g (8.78 mol, 1.0 eq.) of 5-chloro-2-nitropyridine (A2d), 1512 g (17.56 mol, 2.0 eq.) of piperazine (A2c) and 11,340 g (14,000 mL) of n-butanol. The resulting suspension is stirred and heated to 95° C. This temperature is maintained for at least 24 h or until the remaining starting material, A2d, is ≧2% (area normalization) as determined by HPLC analysis. The resulting slurry is cooled to 25° C. over 1 h. The solids are filtered through a polypropylene filter pad. The filter cake is washed twice with a total of 2267 g (2×1300 mL) of isopropyl acetate. The solids are dried at 60° C. for 16 h, to afford 1769 g (82.3%, uncorrected) of A2b as a yellow, crystalline solid, mp>230° C. (dec.).

Workup

  1. customA nitrogen-flushed
  2. temperatureThis temperature is maintained for at least 24 h
  3. temperatureThe resulting slurry is cooled to 25° C. over 1 h
  4. filtrationThe solids are filtered through a polypropylene
  5. filtrationfilter pad
  6. washThe filter cake is washed twice with a total of 2267 g (2×1300 mL) of isopropyl acetate
  7. customThe solids are dried at 60° C. for 16 h
  8. customto afford 1769 g (82.3%, uncorrected) of A2b as a yellow, crystalline solid, mp>230° C. (dec.)

Sources & evidence

ORD record
ord-23eec935e5d7480fb87f872da9788ba9
Source dataset
uspto-grants-2015_11
Patent number
US09193732B2

Reaction notes

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