Cyanoacetamide → Piperidine

HRID 972680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 972680
[Na].[CH3:2][N:3]([CH3:15])[C:4]1[CH:14]=[CH:13][C:7]([C:8]([CH2:10][CH:11]=O)=O)=[CH:6][CH:5]=1.C[O-].[Na+].CN(C)C1C=CC(C(=O)C)=CC=1.C(OCC)=O.[C:36]([CH2:38][C:39]([NH2:41])=[O:40])#[N:37]>O.C(O)(=O)C.O1CCCC1>[NH:3]1[CH2:4][CH2:14][CH2:13][CH2:7][CH2:15]1.[CH3:2][N:3]([CH3:15])[C:4]1[CH:14]=[CH:13][C:7]([C:8]2[NH:41][C:39](=[O:40])[C:38](=[CH:11][CH:10]=2)[C:36]#[N:37])=[CH:6][CH:5]=1

Komponenten

11

Edukt 6

HCID 7898CyanoacetamideHCID 8025Ethyl formateHCID 750374-DimethylaminoacetophenoneHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 126547984-(Dimethylamino)-beta-oxobenzenepropanal

Produkt 2

HCID 8082PiperidineHCID 214045596-[p-(Dimethylamino)phenyl]-1,2-dihydro-2-oxonicotinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

From a solution of the sodium salt of p-(dimethylamino)benzoylacetaldehyde in 400 ml. of water (prepared from 11.4 g. of sodium methoxide in 100 ml. of tetrahydrofuran and a solution of 29.3 g. of p-(dimethylamino)acetophenone [J.A.C.S. 73, 864 (1951)] and 13.3 g. of ethyl formate in 130 ml. of tetrahydrofuran), 18.5 g. of 2-cyanoacetamide and a solution consisting of 2.3 ml. of acetic acid, 5.2 ml. of water and 4.0 ml. of piperidine, there is obtained 6-[p-(dimethylamino)phenyl]-1,2-dihydro-2-oxonicotinonitrile; m.p. 280°-292° (dec.) after crystallization from aqueous dimethyl sulfoxide.

Quellen und Nachweise

ORD-Eintrag
ord-47900b5405bc43558ffeb1bcdee85dfb
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04053470

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