Triethylamine → 4-[(E)-4-Methylpent-2-enoyl]-1-(4-quinolyl)piperazin-2-one

HRID 333935Notes

Reaction equation

HRID 333935 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][C:12]2=[O:17])=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:25][CH:26]([CH3:32])/[CH:27]=[CH:28]/[C:29](Cl)=[O:30]>ClCCl>[CH3:25][CH:26]([CH3:32])/[CH:27]=[CH:28]/[C:29]([N:14]1[CH2:15][CH2:16][N:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[CH:2][CH:3]=2)[C:12](=[O:17])[CH2:13]1)=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10986269(E)-4-methylpent-2-enoyl ChlorideHCID 668359161-(4-Quinolyl)piperazin-2-one

Product 1

HCID 569489634-[(E)-4-Methylpent-2-enoyl]-1-(4-quinolyl)piperazin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(4-Quinolyl)piperazin-2-one (23 mg, 0.1 mmol) was dissolved in dichloromethane (1 ml), triethylamine was added (21 μl, 0.15 mmol) followed by a solution of (E)-4-methylpent-2-enoyl chloride in 0.5 ml dichloromethane. The mixture was shaken briefly, washed with 5% sodium bicarbonate solution (2×), water and evaporated to dryness. The raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile). 14.4 mg of a solid residue were obtained (0.044 mmol, 44%).

Workup

  1. washwashed with 5% sodium bicarbonate solution (2×), water
  2. customevaporated to dryness
  3. customThe raw product was purified by preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile)

Sources & evidence

ORD record
ord-f5ff628303c24337a072d6fb21bc41cd
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Reaction notes

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