1,3-Benzodioxole-5-carboxylic acid → 1-(1,3-Benzodioxol-5-ylcarbonyl)-1,2,3,6-tetrahydro-pyridine

HRID 1458522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1458522
[C:1]([C:8]1NC=CN=1)([C:3]1[NH:4][CH:5]=[CH:6]N=1)=O.[C:13](O)(=[O:23])[C:14]1[CH:22]=[CH:21][C:20]2[O:19][CH2:18][O:17][C:16]=2[CH:15]=1.C(Cl)(=O)C1C=CC2OCOC=2C=1.N1CC=CCC1>>[O:19]1[C:20]2[CH:21]=[CH:22][C:14]([C:13]([N:4]3[CH2:5][CH:6]=[CH:8][CH2:1][CH2:3]3)=[O:23])=[CH:15][C:16]=2[O:17][CH2:18]1

Komponenten

5

Edukt 4

HCID 71961,3-Benzodioxole-5-carboxylic acidHCID 127501,2,3,6-TetrahydropyridineHCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Produkt 1

HCID 117760631-(1,3-Benzodioxol-5-ylcarbonyl)-1,2,3,6-tetrahydro-pyridine

Versuchsvorschrift

The product amide is made by the method employed for the preparation of Invention Compound V, which uses carbonyl diimidazole in order to activate piperonylic acid, or piperonyloyl chloride (available from Aldrich) can be combined with 1,2,3,6-tetrahydropyridine either in a suitable anhydrous solvent or without solvent. In either case, the isolation of product is performed in the same manner as done for Invention Compound V to give Invention Compound III as a white solid. EIMS m/z=231 (parent, 149 (base), and 121. 1H NMR δ 2.21 (br s, 2), 3.4-4.3 (br m, 4), 5.87 (m, 2), 6.00 (s, 2), 6.83 (d, 1, J=7.84 Hz), and 6.92-6.96 (dd and d, 2). 13C NMR δ 101.3 (--OCH2O--) and 169.9 ppm (carbonyl).

Quellen und Nachweise

ORD-Eintrag
ord-7831979740fd4f97a9d3508258c224f9
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852008

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