Trifluoroacetic acid → Dimethyl-(4-piperazin-1-YL-phenyl)-amine

HRID 1647394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647394
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([N:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[CH3:28][N:27]([CH3:29])[C:24]1[CH:23]=[CH:22][C:21]([N:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)=[CH:26][CH:25]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 226678081-(Tert-butoxycarbonyl)-4-(4-dimethylaminophenyl)piperazine

Produkt 1

HCID 4738754Dimethyl-(4-piperazin-1-YL-phenyl)-amineAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (10 ml) was added to a solution of 1-(tert-butoxycarbonyl)-4-(4-dimethylaminophenyl)piperazine (2.01 g 6.58 mmol ) in dichloromethane (20 ml) and the mixture stirred for 30 min at room temperature. The mixture was concentrated in vacuo and saturated aqueous potassium carbonate (100 ml) was cautiously added to the residue. The mixture was extracted with dichloromethane (3×100 ml), the extracts were washed with brine (50 ml), combined and dried (MgSO4). Concentration of the extracts gave 1-(4-dimethylaminophenyl)piperazine (1.14 g, 84%) as a cream solid; δH (DMSO-d6) 2.77 (6H, s, N(CH3)2), 2.79 (4H, m, 2×piperazinyl CH2), 2.86 (4H, m, 2×piperazinyl CH2), 6.68 (2H, m, ArH), and 6.82 (2H, m, ArH).

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo and saturated aqueous potassium carbonate (100 ml)
  2. additionwas cautiously added to the residue
  3. extractionThe mixture was extracted with dichloromethane (3×100 ml)
  4. washthe extracts were washed with brine (50 ml)
  5. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-fcf7bd6b8fd14203bb9d817f1af4f956
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05432177

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