Piperazine → 6-Bromoquipazine

HRID 860009

Reaction equation

HRID 860009 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[CH:6]=[CH:5]2.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>CN(C)C=O.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 4837PiperazineHCID 128940866-Bromo-2-chloroquinoline

Product 1

HCID 1302616-Bromoquipazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-bromo-2-chloroquinoline of Step A (1.25 g, 5.15 mmol) in N,N-dimethylformamide (35 mL) is added piperazine (4.43 g, 51.4 mmol) and the mixture is heated at 110° C. under nitrogen for 3 hours. After cooling, it is diluted with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extracts are dried over anhydrous magnesium sulfate and evaporated to dryness.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracts are dried over anhydrous magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-0968b3c8b57a4bc28a0ab591d4bbdb7e
Source dataset
uspto-grants-2006_12
Patent number
US07153849B2

Linked notes

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