4-Methyl-3-nitroaniline → N-(4-Methyl-3-nitro-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide

HRID 273291

Reaktionsgleichung

Reaktionsgleichung von HRID 273291
C[Al](C)C.[N+:5]([C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][C:14]=1[CH3:15])[NH2:11])([O-:7])=[O:6].C[O:17][C:18](=O)[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]2)=[CH:21][CH:20]=1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C(Cl)Cl.COC(C)(C)C>[CH3:15][C:14]1[CH:13]=[CH:12][C:10]([NH:11][C:18](=[O:17])[C:19]2[CH:20]=[CH:21][C:22]([CH2:25][N:26]3[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]3)=[CH:23][CH:24]=2)=[CH:9][C:8]=1[N+:5]([O-:7])=[O:6]

Komponenten

8

Edukt 4

HCID 83904-Methyl-3-nitroanilineHCID 782222Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoateHCID 9855836Potassium sodium tartarateHCID 16682925Trimethylaluminum

Produkt 1

HCID 29984087N-(4-Methyl-3-nitro-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of trimethylaluminium (2M in toluene, 1.3 ml, 2.6 mmol) is added over a period of 5 min to a solution of 3-nitro-4-methyl-aniline(152 mg, 1.00 mmol) and 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid methyl ester (248 mg, 1.00 mmol) in toluene (3.0 ml) at 45° C. under an atmosphere of argon. After gas evolution ceases, the dark brown reaction mixture is stirred 30 min before being cooled to 0° C. An aqueous saturated solution of potassium-sodium tartrate (20 ml), t-butyl methyl ether (15 ml) and methylene chloride (10 ml) are added sequentially. The organic phase is separated and washed with aqueous saturated NaHCO3 (10 ml) and aqueous saturated NaCl (10 ml). The aqueous phases are back-extracted with t-butyl methyl ether (2×15 ml). The organic phases are combined, dried over MgSO4 and concentrated in vacuo to give 383 mg (96 area % by HPLC) of the title compound as pale yellow crystals.

Aufarbeitung

  1. customThe organic phase is separated
  2. washwashed with aqueous saturated NaHCO3 (10 ml) and aqueous saturated NaCl (10 ml)
  3. extractionThe aqueous phases are back-extracted with t-butyl methyl ether (2×15 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e01e68b5d0e6410ebe169c13eb7d4d6c
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456283B2

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