Piperazine → 7-Chloro-4-(piperazin-1-yl)quinoline

HRID 1500213Notes

Reaction equation

HRID 1500213 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1>CO>[Cl:18][C:14]1[CH:13]=[C:12]2[C:17]([C:8]([N:1]3[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)=[CH:9][CH:10]=[N:11]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 68664,7-Dichloroquinoline

Product 1

HCID 7383897-Chloro-4-(piperazin-1-yl)quinolineYield 115.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An anhydrous solution of piperazine (54 kg) in 150 l of methanol was stirred until a clear solution was obtained. 50 kg 4,7-dichloroquinoline were then slowly added to the solution. The latter was refluxed for 8 hours and cooled to RT. The resulting suspension was filtered and the solvent removed under reduced pressure. The oil obtained was washed with water (150 l) until solid precipitation occurred. The precipitate was filtered and washed with water to yield 72 kg of crystalline 7-chloro-4-(piperazin-1-yl)-quinoline Form B, containing 25% of water (w/w).

Workup

  1. customwas obtained
  2. temperatureThe latter was refluxed for 8 hours
  3. filtrationThe resulting suspension was filtered
  4. customthe solvent removed under reduced pressure
  5. customThe oil obtained
  6. washwas washed with water (150 l) until solid precipitation
  7. filtrationThe precipitate was filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-c3ff2554338b499b913897f5a4d41c55
Source dataset
uspto-grants-2015_12
Patent number
US09206133B2

Reaction notes

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