1,3-Benzodioxole-5-carboxylic acid → 1,3-Benzodioxol-5-yl(3,6-dihydro-1(2H)-pyridinyl)methanone

HRID 442640Notes

Reaction equation

HRID 442640 reaction equation
[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

Participants

5

Reactant 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

Product 1

HCID 117760631,3-Benzodioxol-5-yl(3,6-dihydro-1(2H)-pyridinyl)methanone

Procedure

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).

Sources & evidence

ORD record
ord-24fb296721a34359970fcd166d91a405
Source dataset
uspto-grants-1999_04
Patent number
US05891876

Reaction notes

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