Benzoic acid, 4-fluoro-, ethyl ester → Ethyl 4-(3,4-dimethylpiperazin-1-yl)benzoate

HRID 16766

Reaktionsgleichung

Reaktionsgleichung von HRID 16766
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[CH3:8].F[C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1>CC(N(C)C)=O>[CH3:8][CH:3]1[N:2]([CH3:1])[CH2:7][CH2:6][N:5]([C:10]2[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=2)[CH2:4]1

Komponenten

4

Edukt 2

HCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 198037Dimethylpiperazine

Produkt 1

HCID 57440404Ethyl 4-(3,4-dimethylpiperazin-1-yl)benzoateAusbeute 36,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

1,2-Dimethyl-piperazine (0.914 g, 8.00 mmol) and ethyl 4-fluorobenzoate (0.587 mL, 4 mmol) were dissolved in DMA (6 mL) and sealed into a microwave tube. The reaction was heated to 150° C. for 90 mins in the microwave reactor and cooled to room temperature. The reaction mixture was evaporated and the crude product was purified by silica column chromatography, eluting with 5% MeOH in DCM (containing 0.1% 0.880 ammonia). Pure fractions were evaporated to dryness to afford ethyl 4-(3,4-dimethylpiperazin-1-yl)benzoate (0.380 g, 36.2%) as a colourless waxy solid.

Aufarbeitung

  1. customsealed into a microwave tube
  2. temperaturecooled to room temperature
  3. customThe reaction mixture was evaporated
  4. customthe crude product was purified by silica column chromatography
  5. washeluting with 5% MeOH in DCM (containing 0.1% 0.880 ammonia)
  6. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b9499f38f1d64c97b53dac0a329dbab8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737149B2

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