Sodium Hydroxide → 4-Methyl-1-(2-nitrophenyl)piperazine-2-carboxylic acid

HRID 372198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 372198
[OH-].[Na+].C([O:5][C:6]([CH:8]1[CH2:13][N:12]([CH3:14])[CH2:11][CH2:10][NH:9]1)=[O:7])C.[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1F)([O-:17])=[O:16]>O.C(O)C>[CH3:14][N:12]1[CH2:11][CH2:10][N:9]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N+:15]([O-:17])=[O:16])[CH:8]([C:6]([OH:5])=[O:7])[CH2:13]1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 738951-Fluoro-2-nitrobenzeneHCID 12558522Ethyl 4-methylpiperazine-2-carboxylate

Produkt 1

HCID 203786594-Methyl-1-(2-nitrophenyl)piperazine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of 6.6 g. (0.164 mole) of sodium hydroxide, 28.2 g. (0.165 mole) of ethyl-4-methylpiperazine-2-carboxylate, 20 ml. of water and 200 ml. of ethanol is refluxed for 3 hours. This solution is then added under nitrogen to a hot stirred solution of o-nitrofluorobenzene in 300 ml. of ethanol and 30 ml. of water. The resultant solution is refluxed for 48 hours, cooled and filtered to give 12.8 g. of yellow product, m.p. 222-225°. Concentration of the mother liquors to ~100 ml. and adjusting the pH to 6 yields an additional 6.6 g. of product. Further concentration of mother liquors gives yet another 3 g. of product. Total yield is 22.4 g., 51.5%. The analytical sample had m.p. 234° dec.

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered
  3. customto give 12.8 g
  4. customyields an additional 6.6 g
  5. concentrationFurther concentration of mother liquors
  6. customgives yet another 3 g

Quellen und Nachweise

ORD-Eintrag
ord-a6bcf6bee2cb4a419eff2cd5ac8c8afe
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04089958

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