tert-Butyl 4-formylpiperidine-1-carboxylate → tert-butyl {4-[1-butyl-4,6-di(3-diethylaminopropoxy)-1H-benzimidazol-2-yl]}piperidine-1-carboxylate

HRID 17642

Reaktionsgleichung

Reaktionsgleichung von HRID 17642
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([NH:20][C:21]1[CH:27]=[C:26]([O:28][CH2:29][CH2:30][CH2:31][N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])[CH:25]=[C:24]([O:37][CH2:38][CH2:39][CH2:40][N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[C:22]=1[NH2:23])[CH2:17][CH2:18][CH3:19]>C(O)C>[CH2:16]([N:20]1[C:21]2[CH:27]=[C:26]([O:28][CH2:29][CH2:30][CH2:31][N:32]([CH2:33][CH3:34])[CH2:35][CH3:36])[CH:25]=[C:24]([O:37][CH2:38][CH2:39][CH2:40][N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[C:22]=2[N:23]=[C:14]1[CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1)[CH2:17][CH2:18][CH3:19]

Komponenten

4

Edukt 2

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 669775442-Butylamino-4,6-di(3-diethylaminopropoxy)aniline

Produkt 1

HCID 66977506tert-butyl {4-[1-butyl-4,6-di(3-diethylaminopropoxy)-1H-benzimidazol-2-yl]}piperidine-1-carboxylateAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 1-(t-butyloxycarbonyl)piperdine-4-carboxaldehyde (235 mg; 1.1 mmol) and 2-butylamino-4,6-di(3-diethylaminopropoxy)aniline (synthesized via General Procedures J1 and J2 and I) (424 mg; 1 mmol) in ethanol (5 mL) was subjected to General Procedure K. The crude product was purified by silica gel column chromatography using 10% MeOH in DCM with a gradual increment of triethylamine (0.2 to 1.0%) as eluent to afford 425 mg of tert-butyl {4-[1-butyl-4,6-di(3-diethylaminopropoxy)-1H-benzimidazol-2-yl]}piperidine-1-carboxylate.

Aufarbeitung

  1. customThe crude product was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-64ef82b016524b0e990e1594c8b1277f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737285B2

Verknüpfte Notizen

Wird geladen…