Pyridine → Piperidine

HRID 904879

Reaktionsgleichung

Reaktionsgleichung von HRID 904879
[NH2:1][C:2]1C=C[C:5]([C:6]([CH2:8][C:9]#[N:10])=O)=[CH:4][CH:3]=1.[C:13](#[N:15])C.[N+:16]([CH3:19])([O-])=O.[N:20]1[CH:25]=[CH:24]C=[CH:22][CH:21]=1>C(O)(C)C>[NH:10]1[CH2:4][CH2:5][CH2:6][CH2:8][CH2:9]1.[CH3:2][N:15]([CH3:13])[C:19](=[NH:16])[N:20]([CH3:25])[CH3:21].[CH2:2]1[N:1]2[CH2:22][CH2:21][N:20]([CH2:25][CH2:24]2)[CH2:3]1

Komponenten

8

Edukt 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 6375NitromethaneHCID 96920Benzenepropanenitrile, 4-amino-beta-oxo-

Produkt 3

HCID 8082PiperidineHCID 9237DabcoHCID 664601,1,3,3-Tetramethylguanidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

In accordance with the second procedure, the 4-alkanesulfonaminobenzoylacetonitrile is first prepared by reaction of an alkanesulfonylchloride with 4-amino-benzoylacetonitrile at room temperature in dry pyridine. This product is in turn reacted with a dialkylaminobenzaldehyde at reflux temperature in isopropyl alcohol, acetonitrile, nitromethane, or a similar polar solvent and in the presence of a catalytic amount of piperidine, or another catalyst of comparable basicity such as tetramethylguanidine or triethylenediamine, to yield the desired dye.

Quellen und Nachweise

ORD-Eintrag
ord-f9c4427952c3423b91e2d1a258b32f99
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04420555

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