2,4-Diaminotoluene → 4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethyl-N-(3-amino-4-methylphenyl)benzamide

HRID 13779

Reaktionsgleichung

Reaktionsgleichung von HRID 13779
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH3:9].C(N(C(C)C)CC)(C)C.Cl.Cl.[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][C:30]=2[C:38]([F:41])([F:40])[F:39])[CH2:24][CH2:23]1>CN(C)C1C=CN=CC=1.C(#N)C>[CH3:21][N:22]1[CH2:23][CH2:24][N:25]([CH2:28][C:29]2[CH:37]=[CH:36][C:32]([C:33]([NH:8][C:6]3[CH:5]=[CH:4][C:3]([CH3:9])=[C:2]([NH2:1])[CH:7]=3)=[O:34])=[CH:31][C:30]=2[C:38]([F:41])([F:39])[F:40])[CH2:26][CH2:27]1

Komponenten

6

Edukt 3

HCID 72612,4-DiaminotolueneHCID 81531DiisopropylethylamineHCID 230735454-(4-Methylpiperazin-1-ylmethyl)-3-trifluoromethylbenzoyl chloride dihydrochloride

Produkt 1

HCID 231459584-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethyl-N-(3-amino-4-methylphenyl)benzamideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1.04 g of 2,4-diaminotoluene, 104 mg of 4-(dimethylamino)pyridine and 4.9 ml of N,N-diisopropyl-N-ethylamine were dissolved in 40 ml of acetonitrile. Under ice-cool stirring, 3.70 g of 4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethylbenzoyl chloride dihydrochloride (Reference Example 2) was added by four portions. After stirring for 1 hour, the solvent was distilled off under reduced pressure and diluted with water. The reaction solution was alkalified with an aqueous saturated sodium hydrogen carbonate solution, followed by extraction with ethyl acetate twice, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 2.56 g of the objective compound as a pale brown amorphous.

Aufarbeitung

  1. temperatureUnder ice-cool
  2. stirringAfter stirring for 1 hour
  3. distillationthe solvent was distilled off under reduced pressure
  4. additiondiluted with water
  5. extractionfollowed by extraction with ethyl acetate twice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b7f582fc8d244fbdb46b0a45b6b458da
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728131B2

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