Benzenesulfonyl chloride → N-Benzenesulfonyl-5-(4-methylpiperazin-1-yl)-indole

HRID 2112464

Reaktionsgleichung

Reaktionsgleichung von HRID 2112464
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[CH:11]3)[CH2:4][CH2:3]1.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(Cl)Cl>[C:17]1([S:23]([N:13]2[C:14]3[C:10](=[CH:9][C:8]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:16][CH:15]=3)[CH:11]=[CH:12]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 220154055-(4-Methylpiperazin-1-yl)-1H-indole

Produkt 1

HCID 22015412N-Benzenesulfonyl-5-(4-methylpiperazin-1-yl)-indoleAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-(4-Methylpiperazin-1-yl)-indole (215 mg, 1 mmol), benzenesulfonylchloride (265 mg, 1.5 mmol) and Aliquat 336 (10 mg) were dissolved in DCM (10 mL). Aqueous NaOH (20%, 2 mL) was added and the mixture was stirred vigorously for 6 h. The organic layer was separated, dried and concentrated to give the crude as an oil that was purified on a silica column using DCM and MeOH as eluent. The pure fractions were concentrated to give an oil (260 mg, 0.66 mmol) 1H NMR (CDCl3) δ 2.35 (3H, s), 2.59 (4H, t, J=5), 3.18 (4H, t, J=5), 6.57 (1H, d, J=4), 6.98-7.03 (2H, m), 7.38-7.54 (4H, m), 7.82-7.90 (3H, m); MS (posES-FIA) 355.1345 M+; Purity (HPLC chromsil C18) >98%.

Aufarbeitung

  1. customThe organic layer was separated
  2. customdried
  3. concentrationconcentrated
  4. customto give the crude as an oil that
  5. customwas purified on a silica column
  6. concentrationThe pure fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-c30c7a31efb84a4cb3f1baac90567d54
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07524839B2

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