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

HRID 2052081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2052081
[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-10b3d7adc0764225b66a20bfcf4d013c
Quelldatensatz
uspto-grants-1980_01
Patentnummer
US04182869

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