Hydrochloric Acid → Diethyl 2-methyl-2-(4-(piperazin-1-yl)phenyl)malonate

HRID 1896270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896270
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:19])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.Cl[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]Cl.Cl>C1(C)C(C)=CC=CC=1>[CH3:19][C:8]([C:5]1[CH:6]=[CH:7][C:2]([N:1]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:3][CH:4]=1)([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 9533Bis(2-chloroethyl)amineHCID 12370795HCID 12370795, Verbindung

Produkt 1

HCID 67382666Diethyl 2-methyl-2-(4-(piperazin-1-yl)phenyl)malonateAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A suspension of diethyl 2-(4-aminophenyl)-2-methylmalonate (6.00 g, 22.6 mmol), Bis-(2-chloroethyl) amine.HCl (4.82 g, 27.2 mmol) in xylene (20 ml) was refluxed for 48 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate. The separated organic layer was washed with water, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford crude product. Purification by column chromatography over neutral alumina using 5% MeOH in CHCl3 as eluent afford 4.80 g (63.5%) of diethyl 2-methyl-2-(4-(piperazin-1-yl)phenyl)malonate as brown oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate
  3. washThe separated organic layer was washed with water, brine solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude product
  8. customPurification by column chromatography over neutral alumina using 5% MeOH in CHCl3 as eluent

Quellen und Nachweise

ORD-Eintrag
ord-1c7ea67d264d417db8234e9a5046e4fe
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518948B2

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