Triethylamine → N-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]4-nitrobenzamide hydrochloride

HRID 413977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 413977
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16][NH2:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([Cl:28])=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20].C(N(CC)CC)C>C(Cl)Cl>[ClH:28].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16][NH:17][C:26](=[O:27])[C:25]2[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:30][CH:29]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 104449491,3-Propanediamine, N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-

Produkt 1

HCID 70011353N-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]4-nitrobenzamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

800 mg (3.17 mmol) N-[2-(3,4-Dimethoxyphenyl)ethyl]-N-methyl-1,3-propanediamine (D2), 630 mg (3.33 mmol) 4-nitro benzoyl chloride and 0.35 g (3.49 mmol) triethylamine in 30 ml methylene chloride were stirred for 2 hours at room temperature. The mixture was washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified twice by chromatography on silicagel using methylene chloride/methanol: 97/3 then 94/6 yielding 700 mg (55%) of the desired compound as a base. The compound was salified in methylene chloride by adding a solution of hydrochoric acid in diethyl ether yielding 594 mg (43%) of the desired compound as a yellow solid: mp =80-90° C.

Aufarbeitung

  1. washThe mixture was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified twice by chromatography on silicagel
  5. additionby adding a solution of hydrochoric acid in diethyl ether yielding 594 mg (43%) of the desired compound as a yellow solid
  6. custommp =80-90° C.

Quellen und Nachweise

ORD-Eintrag
ord-d6eae474955f41c498ddd5ef34d0c9de
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06570037B2

Notizen zur Reaktion

Wird geladen…