2-Chloro-4-nitrobenzoic acid → N-tert-Butyl-3-((4-(2-chloro-4-nitrobenzoyl)piperazin-1-yl)methyl)benzamide

HRID 1878344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1878344
CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.[Cl:19][C:20]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:21]=1[C:22]([OH:24])=O.[C:32]([NH:36][C:37](=[O:51])[C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[CH:39]=1)([CH3:35])([CH3:34])[CH3:33].C(N(CC)CC)C>ClCCl>[C:32]([NH:36][C:37](=[O:51])[C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][N:45]2[CH2:46][CH2:47][N:48]([C:22](=[O:24])[C:21]3[CH:25]=[CH:26][C:27]([N+:29]([O-:31])=[O:30])=[CH:28][C:20]=3[Cl:19])[CH2:49][CH2:50]2)[CH:39]=1)([CH3:35])([CH3:33])[CH3:34]

Komponenten

6

Edukt 4

HCID 74482-Chloro-4-nitrobenzoic acidHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 66877987N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide

Produkt 1

HCID 57917601N-tert-Butyl-3-((4-(2-chloro-4-nitrobenzoyl)piperazin-1-yl)methyl)benzamideAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Propanephosphonic acid cyclic anhydride (3.16 g, 92 mmol, 2.95 mL) was added dropwise to a solution of 2-chloro-4-nitrobenzoic acid (1 g, 4.9 mmol), N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide (1.4169 g, 5.1 mmol) and triethylamine (1.4979 g, 14.7 mmol, 2 mL) in dichloromethane. The reaction was concentrated under reduced pressure and the residue was taken up in ethyl acetate, washed with water, sodium hydrogen carbonate and brine. The organic phase was concentrated under vacuum to afford the title compound (2.06 g).

Aufarbeitung

  1. concentrationThe reaction was concentrated under reduced pressure
  2. washwashed with water, sodium hydrogen carbonate and brine
  3. concentrationThe organic phase was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-bcdefdd8a9b44da38ebdc4eb3c3c7828
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314091B2

Notizen zur Reaktion

Wird geladen…