t-butyl 4-(1-benzenesulfonyl-1H-indol-4-yl)piperazine-1-carboxylate → 1-(Phenylsulfonyl)-4-(1-piperazinyl)-1h-indole

HRID 1006421

Reaktionsgleichung

Reaktionsgleichung von HRID 1006421
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O>[C:26]1([S:23]([N:18]2[C:19]3[C:15](=[C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:22]=[CH:21][CH:20]=3)[CH:16]=[CH:17]2)(=[O:25])=[O:24])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Komponenten

3

Edukt 1

HCID 22015366t-butyl 4-(1-benzenesulfonyl-1H-indol-4-yl)piperazine-1-carboxylate

Produkt 1

HCID 101543921-(Phenylsulfonyl)-4-(1-piperazinyl)-1h-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of 125 mg (0.28 mmole) 4-(1-benzenesulfonyl-1H-indol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester in 2 mL trifluoroacetic acid was stored at room temperature for 10 minutes. The solution was concentrated under reduced pressure and the residue was partitioned between 3 mL 10% sodium carbonate and 20 mL ethyl acetate. The organic phase was washed with 5 mL water, dried (magnesium sulfate) and concentrated. 1-Benzenesulfonyl-4-piperazin-1-yl-1H-indole (5) was isolated as the hydrochloride salt from ethyl acetate-ethyl ether, 73 mg, M+H=342; m.p.294-295° C.

Aufarbeitung

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe residue was partitioned between 3 mL 10% sodium carbonate and 20 mL ethyl acetate
  3. washThe organic phase was washed with 5 mL water
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-739071936fc645228785cdc460a703e5
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06790848B2

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