Triethylamine → HCID 135782141, Verbindung

HRID 1905631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1905631
C([N:3]([CH2:6][CH3:7])CC)C.Cl.Cl.[CH2:10]([N:17]1[CH2:22][CH2:21][C:20]([NH2:26])([C:23](Cl)=[O:24])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N1CCC(N)(C(O)=O)CC1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[OH-].[Na+]>C(Cl)Cl.C(Cl)CCl>[CH3:31][C:32]1[C:33]2[CH:28]=[CH:29][CH:30]=[CH:7][C:6]=2[NH:3][C:23](=[O:24])[C:20]2([CH2:21][CH2:22][N:17]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:18][CH2:19]2)[N:26]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 14803624-Amino-1-benzylpiperidine-4-carboxylic AcidHCID 88658736HCID 88658736, Verbindung

Produkt 1

HCID 135782141HCID 135782141, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 12.2 g (0.12 mole) of triethylamine in 100 ml of methylene chloride is added dropwise to a mixture of 5.4 g (0.04 mole) of 2-aminocetophenone and 13.0 g (0.04 mole) of 1-benzyl-4-amino-4-piperidine-carboxylic acid chloride dihydrochloride (prepared from 9.4 g (0.04 mole) of 1-benzyl-4-amino-4-carboxypiperidine by reaction with excess phosphorus-V chloride in methylene chloride at 25° C.) in 400 ml of ethylene chloride at 0° C., while stirring and under an N2 atmosphere, and the mixture is stirred at 0° C. for 1 hour and finally at 25° C. for 2 hours. It is then poured onto ice, the pH is brought to 10 with sodium hydroxide solution and the reaction product is extracted with methylene chloride. For purification, the product is chromatographed on silica gel 60 (Merck), a methylene chloride/methanol mixture (10:1) being used as the eluting agent.

Aufarbeitung

  1. stirringthe mixture is stirred at 0° C. for 1 hour and finally at 25° C. for 2 hours
  2. additionIt is then poured onto ice
  3. extractionthe reaction product is extracted with methylene chloride
  4. customFor purification
  5. customthe product is chromatographed on silica gel 60 (Merck)

Quellen und Nachweise

ORD-Eintrag
ord-d9f09585cac048b89ef6eed536373772
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04647560

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