Triethylamine → HCID 31096158, compound

HRID 1889005Notes

Reaction equation

HRID 1889005 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].C(N(CC)CC)C.[CH3:15][C:16]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19]>ClCCl>[CH3:15][C:16]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:17]=1[C:18]([N:4]1[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]1)=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1408672,4-Dimethylbenzoyl chlorideHCID 231360Piperazin-2-one

Product 1

HCID 31096158HCID 31096158, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-piperazinone (0.851 g, 8.5 mmol, commercially available from e.g. Sigma-Aldrich) was dissolved in dichloromethane (DCM) (30 mL), and to this was added triethylamine (1.422 mL, 10.20 mmol). The solution was then cooled to 0° C. before 2,4-dimethylbenzoyl chloride (I53) (1.577 g, 9.35 mmol) in dichloromethane (DCM) (5 mL) was added dropwise. The solution was stirred, under argon, for 30 minutes before the solvent was evaporated in vacuo. The remaining residue was then dissolved in DCM (40 mL) and the solution was washed with water (20 mL), a saturated solution of sodium bicarbonate (20 mL) and brine (20 mL). The organic phase was then dried over anhydrous sodium sulphate, and the solid sodium sulphate was then filtered off. The solvent was then evaporated in vacuo, and the remaining solid was stirred in hexane, at 55° C., for 30 minutes. The solid was then filtered, and analysis by LCMS showed impurities still to be present. The solid was thus further purified by flash chromatography (Isolera 100 g cartridge) with a gradient of 0-10% MeOH in DCM. TLC confirmed product location and the solvent from the combined fractions was evaporated in vacuo to yield the product in 1.482 g.

Workup

  1. additionwas added dropwise
  2. customwas evaporated in vacuo
  3. dissolutionThe remaining residue was then dissolved in DCM (40 mL)
  4. washthe solution was washed with water (20 mL)
  5. dry with materialThe organic phase was then dried over anhydrous sodium sulphate
  6. filtrationthe solid sodium sulphate was then filtered off
  7. customThe solvent was then evaporated in vacuo
  8. stirringthe remaining solid was stirred in hexane, at 55° C., for 30 minutes
  9. filtrationThe solid was then filtered
  10. customThe solid was thus further purified by flash chromatography (Isolera 100 g cartridge) with a gradient of 0-10% MeOH in DCM
  11. customthe solvent from the combined fractions was evaporated in vacuo
  12. customto yield the product in 1.482 g

Sources & evidence

ORD record
ord-5ee2f3ad76b541619f18bed30f7dcdf7
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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