Tris(hydroxymethyl)aminomethane → N-(3,4-Dichlorophenyl)piperazine-1-carboxamide

HRID 603211

Reaktionsgleichung

Reaktionsgleichung von HRID 603211
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[N:12]1(C(OC(C)(C)C)=O)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(O)C(N)(CO)CO>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

5

Edukt 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 76073,4-Dichlorophenyl isocyanateHCID 143452tert-Butyl piperazine-1-carboxylate

Produkt 1

HCID 16775732N-(3,4-Dichlorophenyl)piperazine-1-carboxamideAusbeute 109,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

3,4-Dichlorophenylisocyanate (3.43 g) and tert-butyl piperazine-1-carboxylate (3.40 g) were stirred for 18 hours in chloroform (20 ml) at room temperature. Trisamine resin (1 g) was added and the mixture stirred for 3 hours, then filtered off. Trifluoroacetic acid (10 ml) was added to the filtrate and this mixture was stirred for two hours. The reaction mixture was concentrated in vacuo and the resulting oil separated between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate solution (100 ml). The ethyl acetate layer was separated, dried over magnesium sulphate, filtered then concentrated in vacuo to give the title compound (5.47 g).

Aufarbeitung

  1. filtrationfiltered off
  2. additionTrifluoroacetic acid (10 ml) was added to the filtrate
  3. stirringthis mixture was stirred for two hours
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe resulting oil separated between ethyl acetate (100 ml) and saturated aqueous sodium bicarbonate solution (100 ml)
  6. customThe ethyl acetate layer was separated
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationthen concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bb55d5fb31c243d4a8c39b32098b37c5
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906645B2

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