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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18945197, Verbindung

HRID 399809
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 399809
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH:13]=1)[C:8]([OH:10])=O)=[O:4].[OH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>ClCCl>[OH:19][CH:20]1[CH2:25][CH2:24][N:23]([C:8]([C:7]2[CH:6]=[C:5]([CH:13]=[C:12]([N:14]3[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH:11]=2)[C:3]([O:2][CH3:1])=[O:4])=[O:10])[CH2:22][CH2:21]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 79341Piperidin-4-olHCID 18945316HCID 18945316, Verbindung

Produkt 1

HCID 18945197HCID 18945197, VerbindungAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a mixture of 3-methoxycarbonyl-5-(pyrrol-1-yl)-benzoic acid (3.0 g), 4-hydroxypiperidine (1.23 g) and 1-hydroxybenzotriazole (1.81 g) in dichloromethane (100 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (2.57 g) under ice cooling, and the solution was stirred for 30 hours at room temperature. After evaporating the solvent, the residue was dissolved in a mixture of ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution under stirring. The organic layer was successively washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (50:1). The fractions containing the desired product were collected and evaporated in vacuo to afford methyl 3-[(4-hydroxypiperidin-1-yl)carbonyl]-5-(pyrrol-1-yl)benzoate (3.56 g).

Aufarbeitung

  1. customAfter evaporating the solvent
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate
  3. stirringa saturated aqueous sodium hydrogencarbonate solution under stirring
  4. washThe organic layer was successively washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (50:1)
  8. additionThe fractions containing the desired product
  9. customwere collected
  10. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6f02db630cdf43c2ab9c7aaa6432c167
Quelldatensatz
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05824691

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