Triethylamine → 4-(4-Methoxybenzyl)-3,3-dimethyl-piperazin-2-one

HRID 43139

Reaktionsgleichung

Reaktionsgleichung von HRID 43139
[CH3:1][C:2]1([CH3:9])[NH:7][CH2:6][CH2:5][NH:4][C:3]1=[O:8].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:7]2[CH2:6][CH2:5][NH:4][C:3](=[O:8])[C:2]2([CH3:9])[CH3:1])=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 1650214-Methoxybenzyl bromide2×HCID 2111572-Piperazinone, 3,3-dimethyl-

Produkt 1

HCID 669145564-(4-Methoxybenzyl)-3,3-dimethyl-piperazin-2-oneAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3,3-dimethyl-piperazin-2-one (Step 108.4) (3.7 g, 28.9 mmol), 4-methoxybenzyl bromide (5.4 mL, 37.6 mmol, 1.3 equiv) and triethylamine (5.2 mL, 37.6 mmol, 1.3 equiv) in DCM (60 mL) was stirred for 48 h at rt. Additional 5.0 mL of 4-methoxybenzyl bromide were added and the mixture was stirred for 72 h at rt, then concentrated. The residue was diluted with DCM/saturated aqueous solution of NaHCO3. The aqueous phase was separated and extracted with DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was triturated in DCM to provide 3.95 g of the title compound as a white solid: ESI-MS: 249.2 [M+H]+; TLC: Rf=0.16 (Hex/EtOAc, 2:3).

Aufarbeitung

  1. stirringthe mixture was stirred for 72 h at rt
  2. concentrationconcentrated
  3. additionThe residue was diluted with DCM/saturated aqueous solution of NaHCO3
  4. customThe aqueous phase was separated
  5. extractionextracted with DCM
  6. washThe organic phase was washed with H2O and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was triturated in DCM

Quellen und Nachweise

ORD-Eintrag
ord-7b7a491c70364dd0b9a78595a9ed8db0
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536175B2

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