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Water → N-[3-(3,4,5-trimethoxyphenyl)benzoyl]-N'-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperazine

HRID 1267667
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1267667
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[C:17]([CH2:19][N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:16]=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:26][O:27][C:28]1[CH:29]=[C:30]([C:38]2[CH:39]=[C:40]([CH:44]=[CH:45][CH:46]=2)[C:41](O)=[O:42])[CH:31]=[C:32]([O:36][CH3:37])[C:33]=1[O:34][CH3:35].C(N(CC)CC)C.O>CN(C)C1C=CN=CC=1.ClCCl>[CH3:37][O:36][C:32]1[CH:31]=[C:30]([C:38]2[CH:39]=[C:40]([CH:44]=[CH:45][CH:46]=2)[C:41]([N:23]2[CH2:24][CH2:25][N:20]([CH2:19][C:17]3[CH:16]=[CH:15][N:14]=[C:13]([C:5]4[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:18]=3)[CH2:21][CH2:22]2)=[O:42])[CH:29]=[C:28]([O:27][CH3:26])[C:33]=1[O:34][CH3:35]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 120211551-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]-methyl]piperazineHCID 225580663-(3,4,5-Trimethoxyphenyl)benzoic acid

Produkt 1

HCID 18546841N-[3-(3,4,5-trimethoxyphenyl)benzoyl]-N'-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl]-piperazine (226 mg), 3-(3,4,5-trimethoxyphenyl)benzoic acid (173 mg) and 4-(dimethylamino)pyridine (61 mg) were dissolved in dichloromethane (3 mL), and triethylamine (2.1 μL) was added to the solution. Water-soluble carbodiimide hydrochloride (115 mg) was added to the mixture at 0° C., and the resultant mixture was stirred for 2 hours at 0° C. and overnight at room temperature. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the resultant mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=40:1) to obtain the title compound as a free base.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  2. additionwas added to the residue
  3. washthe resultant mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-f2cd371598c64c109e37a4cc5ddc6931
Quelldatensatz
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06552188B2

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