4-Piperazin-1-yl-quinoline → (E)-4-Bromo-1-[4-(4-quinolyl)piperazin-1-yl]pent-2-en-1-one

HRID 333951Notes

Reaction equation

HRID 333951 reaction equation
[N:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Br:17][CH:18]([CH3:24])/[CH:19]=[CH:20]/[C:21](Cl)=[O:22]>ClCCl>[Br:17][CH:18]([CH3:24])/[CH:19]=[CH:20]/[C:21]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3]1)=[O:22]

Participants

4

Reactant 2

HCID 15343864-Piperazin-1-yl-quinolineHCID 13043693(E)-4-bromopent-2-enoyl chloride

Product 1

HCID 66835940(E)-4-Bromo-1-[4-(4-quinolyl)piperazin-1-yl]pent-2-en-1-oneYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-piperazin-1-ylquinoline (21.3 mg, 0.1 mmol) was dissolved in anhydrous dichloromethane (0.5 ml), TEA (20.9 μl, 1.5 mmol) followed by (E)-4-bromopent-2-enoyl chloride (29.6 mg, 0.15 mmol) were added, the mixture was shaken for 10 minutes, diluted with dichloromethane, washed with 5% sodium bicarbonate solution, water and the organic phase was evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 7 mg of a solid (0.019 mmol, 19%).

Workup

  1. additionwere added
  2. washwashed with 5% sodium bicarbonate solution, water
  3. customthe organic phase was evaporated to dryness under reduced pressure
  4. customThe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)

Sources & evidence

ORD record
ord-94bb8e4dfc2148afa71bd97c62d3e821
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Reaction notes

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