Toluene → HCID 18940674, Verbindung

HRID 355751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 355751
[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.C1(C)C=CC=CC=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][C:30]=1[N:36]1[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]1>ClCCl.C(N(CC)CC)C>[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:11](=[O:13])[C:10]2[CH:9]=[CH:8][C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[CH:15][CH:14]=2)=[CH:31][C:30]=1[N:36]1[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH2:41]1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 883374-Cyclohexylbenzoic acidHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

Produkt 1

HCID 18940674HCID 18940674, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4-Cyclohexylbenzoic acid (300 mg, 1.5 mmol) was heated at reflux with thionyl chloride (2 ml) and toluene (40 ml) for 2 h, and then evaporated to dryness under reduced pressure. 4-Methoxy-3-(4-methyl-1-piperazinyl)phenylamine (325 mg, 1.5 mmol) in dry dichloromethane (40 ml) was added with triethylamine (2 ml) and the mixture stirred for 1 h. The solution was partitioned between dichloromethane (40 ml) and saturated aqueous potassium carbonate (40 ml), the organic solution dried (sodium sulphate) and evaporated to dryness under reduced pressure to afford an oil, which was purified by flash column chromatography (silica, chloroform/methanol 5%) to afford the title compound (561 mg, 92%) which was crystallised from methanol/diethyl ether as the oxalate salt m.p. 117°-119° C.

Aufarbeitung

  1. customevaporated to dryness under reduced pressure
  2. customThe solution was partitioned between dichloromethane (40 ml) and saturated aqueous potassium carbonate (40 ml)
  3. dry with materialthe organic solution dried (sodium sulphate)
  4. customevaporated to dryness under reduced pressure
  5. customto afford an oil, which
  6. customwas purified by flash column chromatography (silica, chloroform/methanol 5%)

Quellen und Nachweise

ORD-Eintrag
ord-b49adb1682b84888bb73f304ad919862
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834471

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