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Hydrochloric Acid → (+/-)-1,4-Bis(diphenylcarbamoyl)piperazine2-carboxylic acid

HRID 486751
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 486751
[C:1]1([N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH:20]1[C:25]([OH:27])=[O:26].[OH-:28].[Na+].Cl>C(#N)C>[C:1]1([N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([N:19]2[CH2:24][CH2:23][N:22]([C:8](=[O:28])[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:21][CH:20]2[C:25]([OH:27])=[O:26])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 65741N,N-Diphenylcarbamic chlorideHCID 2723757Piperazine-2-carboxylic acid dihydrochloride

Produkt 1

HCID 22004705(+/-)-1,4-Bis(diphenylcarbamoyl)piperazine2-carboxylic acidAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

A solution of 946 mg (4 mmole) of 98% diphenylcarbamoyl chloride in 4 ml of acetonitrile was added dropwise to a stirring solution of 406.2 mg (2 mmole) of piperazine-2-carboxylic acid dihydrochloride [E. Felder, S. Maffei, S. Pietra and D. Pitre, Helv. Chim., Acta. 43, 888 (1960)] in 4 ml of 2.5N-sodium hydroxide at a temperature between 0° and 5° C. After the addition was completed, the stirring was continued for 4 hours and the solution was acidified with 2N-hydrochloric acid while cooling in an ice bath. The reaction mixture was concentrated under reduced pressure and the residue was extracted with chloroform. After washing with water, the chloroform solution was dried over MgSO4 and concentrated in vacuo. The only product which solidified on cooling was triturated with isopropyl ether to give 270 mg (26%) of (±)-1,4-bis(diphenylcarbamoyl)piperazine2-carboxylic acid, m.p. 244°-246° C.

Aufarbeitung

  1. additionAfter the addition
  2. temperaturewhile cooling in an ice bath
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. washAfter washing with water
  6. dry with materialthe chloroform solution was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. temperatureon cooling
  9. customwas triturated with isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e4ed22f95ff544038c73676c772e5fa1
Quelldatensatz
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05292726

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