Potassium Carbonate → ethyl-2-{1-[3-(4-methylpiperazin-1-yl)propyl]-1H-indol-3-yl}-2-oxoacetate

HRID 1472938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1472938
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1.[CH2:12]([O:14][C:15](=[O:27])[C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1)=[O:17])[CH3:13].C([O-])([O-])=O.[K+].[K+]>>[CH2:12]([O:14][C:15](=[O:27])[C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([CH2:2][CH2:3][CH2:4][N:5]2[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]2)[CH:19]=1)=[O:17])[CH3:13]

Komponenten

4

Edukt 3

HCID 11430Potassium CarbonateHCID 669061-(3-Chloropropyl)-4-methylpiperazineHCID 101242Ethyl 3-indolylglyoxylate

Produkt 1

HCID 67255268ethyl-2-{1-[3-(4-methylpiperazin-1-yl)propyl]-1H-indol-3-yl}-2-oxoacetateAusbeute 53 %

Versuchsvorschrift

The general procedure 1 was then followed using 1-(3-chloropropyl)-4-methylpiperazine (12.5 mmol, 2.2 g), ethyl-2-(1H-indol-3-yl)-2-oxoacetate (10 mmol, 2.17 g) and K2CO3 (10.8 mmol, 1.5 g). The purification was achieved by column chromatography (petro-lether:ethylacetate:diethylamine 5:5:1) to yield ethyl-2-{1-[3-(4-methylpiperazin-1-yl)propyl]-1H-indol-3-yl}-2-oxoacetate (5.3 mmol, 42%). IR [cm−1]=2936; 2790; 1727; 1638. FD-MS m/z (rel. int.)=359.9 (2.05%; M+•.). 1H NMR (300 MHz, CDCl3) 8.40 (m; 2H; indole-H); 7.36 (m; 3H; indole-H); 4.38 (q; 3J=7.1 Hz; 2H; OCH2CH3); 4.25 (t; 3J=6.5 Hz; 2H; indole-CH2CH2CH2N); 2.44 (m; 8H; 4× piperazin-CH2); 2.30 (s; 3H; CH3); 2.26 (t; 3J=6.5 Hz; 2H; indole-CH2CH2CH2N); 2.00 (m; 2H;

Aufarbeitung

  1. customThe purification

Quellen und Nachweise

ORD-Eintrag
ord-eeef87dc544c4563a94a6658ec68edc5
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012659B2

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