StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-amino-5-chloro-N-((4-hydroxy-1-(6-oxo-6-phenylhexyl)-piperidin-4-yl)methyl)-2-methoxybenzamide

HRID 344533
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 344533
Cl.Cl.[NH2:3][CH2:4][C:5]1([OH:24])[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:7][CH2:6]1.[NH2:25][C:26]1[C:34]([Cl:35])=[CH:33][C:29]([C:30](O)=[O:31])=[C:28]([O:36][CH3:37])[CH:27]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(N(CC)CC)C>[NH2:25][C:26]1[C:34]([Cl:35])=[CH:33][C:29]([C:30]([NH:3][CH2:4][C:5]2([OH:24])[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:23])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:7][CH2:6]2)=[O:31])=[C:28]([O:36][CH3:37])[CH:27]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 700755654-Aminomethyl-4-hydroxy-1-(6-oxo-6-phenylhexyl)piperidine dihydrochloride

Produkt 1

HCID 538753744-amino-5-chloro-N-((4-hydroxy-1-(6-oxo-6-phenylhexyl)-piperidin-4-yl)methyl)-2-methoxybenzamide
Ausbeute 79,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 4-aminomethyl-4-hydroxy-1-(6-oxo-6-phenylhexyl)-piperidine dihydrochloride (2.9 g) in dimethylformamide (50 ml) were added triethylamine (3.2 ml), 4-amino-5-chloro-2-methoxybenzoic acid (1.55 g) and 1-hydroxybenzotriazole (1.09 g), which was followed by the addition of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.55 g) under ice cooling, and the mixture was stirred at room temperature for 6 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was added with water and extracted with chloroform. The organic layer was washed successively with 10% aqueous solution of potassium carbonate and brine, and dried. The solvent was evaporated under reduced pressure, and the obtained residue was purified by a silica gel column chromatography (chloroform:methanol=10:1) to give 2.98 g of 4-amino-5-chloro-N-((4-hydroxy-1-(6-oxo-6-phenylhexyl)-piperidin-4-yl)methyl)-2-methoxybenzamide.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe obtained residue was added with water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed successively with 10% aqueous solution of potassium carbonate and brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by a silica gel column chromatography (chloroform:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-28d3af8d28244930a991f8d81b245910
Quelldatensatz
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05864039

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion