Potassium Carbonate → 4-[3-(6,7-Dimethoxy-3-styryl-quinoxalin-2-ylamino)-propyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1250235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1250235
Cl[C:2]1[C:11]([CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:10][C:9]2[C:4](=[CH:5][C:6]([O:22][CH3:23])=[C:7]([O:20][CH3:21])[CH:8]=2)[N:3]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([CH2:37][CH2:38][CH2:39][NH2:40])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.CCOC(C)=O>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([CH2:37][CH2:38][CH2:39][NH:40][C:2]2[C:11]([CH:12]=[CH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:10][C:9]3[C:4](=[CH:5][C:6]([O:22][CH3:23])=[C:7]([O:20][CH3:21])[CH:8]=3)[N:3]=2)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 22990164tert-Butyl 4-(3-aminopropyl)piperidine-1-carboxylateHCID 734373392-Chloro-6,7-dimethoxy-3-styryl-quinoxaline

Produkt 1

HCID 701643374-[3-(6,7-Dimethoxy-3-styryl-quinoxalin-2-ylamino)-propyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture 2-chloro-6,7-dimethoxy-3-styryl-quinoxaline (see Kadin, S. B., Ger Offen., DE 2357186; 255 mg, 0.78 mmol), 4-(3-amino-propyl)-piperidine-1-carboxylic acid tert-butyl ester (see Egbertson, M, U.S. Pat. No. 5494921; 392 mg, 1.6 mmol) and potassium carbonate (220 mg, 1.6 mmol) was heated at 120° C. in DMSO (2 mL) for 17 h. After cooling to room temperature, the reaction mixture was diluted with EtOAc and washed with sat'd aq NaHCO3, sat'd aq NaCl, dried and concentrated under vacuum. The crude residue was chromatographed on SiO2-gel to give 150 mg of a yellow oil. API-MS: 533 (M+1). 1H NMR (300 MHz, CDCl3): d 7.75 (d, 1 H), 7.58 (d, 1 H), 7.35 (m), 7.15 (d, 1 H), 4.05 (m), 3.99 (s, 3 H), 3.97 (s, 3 H), 3.54 (bs, 1 H), 2.68 (t, 2 H),1.75 (m), 1.42 (s, 9 H), 1.1 (m).

Aufarbeitung

  1. washwashed with sat'd aq NaHCO3
  2. customdried
  3. concentrationconcentrated under vacuum
  4. customThe crude residue was chromatographed on SiO2-gel

Quellen und Nachweise

ORD-Eintrag
ord-31ce23313443412a9c9bad6cbbe15daf
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06337332B1

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