Reaktion #9495

ord-49ad03b0f69c45cab1df976518211e4d

Reaktionsgleichung

O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl
4-Chloro-3-nitro-7-phenylquinoline
CC(C)(C)OC(=O)N1CCC(CN)CC1
1-(tert-butoxycarbonyl)-4-(aminomethyl)piperidine
CC(C)(C)OC(=O)N1CCC(CNc2c([N+](=O)[O-])cnc3cc(-c4ccccc4)ccc23)CC1
tert-butyl 4-[(3-nitro-7-phenylquinolin-4-ylamino)methyl]piperidine-1-carboxylate
Ausbeute 94.3%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe crude solid was triturated with water
  2. 2
    Sonstigeisolated by filtration
  3. 3
    Sonstigeisolated by filtration
  4. 4
    Sonstigedried for four hours in a vacuum oven at 40° C.

Vorschrift

4-Chloro-3-nitro-7-phenylquinoline (8.35 g, 29.3 mmol) was treated with 1-(tert-butoxycarbonyl)-4-(aminomethyl)piperidine (7.54 g, 35.2 mmol) according to the method described in Part A of Examples 152–156. The crude solid was triturated with water, isolated by filtration, sonicated with diethyl ether, isolated by filtration, and dried for four hours in a vacuum oven at 40° C. to provide 12.78 g of tert-butyl 4-[(3-nitro-7-phenylquinolin-4-ylamino)methyl]piperidine-1-carboxylate as a yellow solid, mp 153–154° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07091214B2uspto-grants-2006_08