Water → Benzyl 4-(naphthalen-2-ylsulfonyl)piperazine-1-carboxylate

HRID 516999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516999
Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[S:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:14])=[O:13].N1C=CC=CC=1.[C:27](Cl)([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].O>C(Cl)Cl>[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:17][CH2:16]1)(=[O:14])=[O:13]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 10387Benzyl chloroformateHCID 227218151-(Naphthalene-2-sulfonyl)piperazine hydrochloride2×

Produkt 1

HCID 66847628Benzyl 4-(naphthalen-2-ylsulfonyl)piperazine-1-carboxylateAusbeute 50,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a two neck round bottom flask, 1-(naphthalene-2-ylsulfonyl)piperazine hydrochloride (compound 4, 0.72 mmoles, 0.200 g) and pyridine (7.22 mmoles, 2 mL) were charged in DCM (20 mL) at 0° C. CBZCl (1.08 mmoles, 0.30 g) was added slowly at the same temperature and then allowed the reaction mixture to stir for 3 h at room temperature. After completion of the reaction, water (10 mL) was added and extracted with DCM (2×20 mL). The combined organic layers were washed with brine (1×20 mL), dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by Column Chromatography (Silica gel 60-120, MeOH/DCM) to obtain the title compound (0.150 g, 50.6%) as an off-white solid.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with DCM (2×20 mL)
  3. washThe combined organic layers were washed with brine (1×20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by Column Chromatography (Silica gel 60-120, MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-df7945fc9dd4478997cf08b28e1c7008
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115086B2

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