ChemicalBook CAS DataBase List 5,6-Dimethoxy-2-(piperidin-4-yl)methylene-indan-1-one

5,6-Dimethoxy-2-(piperidin-4-yl)methylene-indan-1-one synthesis

7synthesis methods

Product Name:5,6-Dimethoxy-2-(piperidin-4-yl)methylene-indan-1-one
CAS Number:120014-30-4
Molecular formula:C17H23NO3
Molecular Weight:289.37

120014-06-4 Synthesis

120014-06-4
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5,6-Dimethoxy-2-(piperidin-4-yl)methylene-indan-1-one

120014-30-4
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$300.00/100g

Yield:120014-30-4 97%

Reaction Conditions:

with ammonium formate;palladium 10% on activated carbon in methanol at 20; for 3 h;Heating / reflux;

Steps:

1; 4 Synthesis of 5,6-dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one 12 (Scheme 4)
Example 1 Synthesis of 5,6-dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one 12 (Scheme 4) To a stirred suspension of palladium, 10 wt. % on activated carbon (4 g) in methanol (25 ml) at room temperature under nitrogen atmosphere was added a solution of indanone 11 (0.01 mol, 4.1 g) in methanol (25 ml) followed by ammonium formate (0.07 mol, 4.40 g). The resulting mixture was refluxed for 3 hours. The progress of the reaction was monitored by TLC. The reaction mixture was cooled to room temperature and filtered through a Celite pad. The filtrate was concentrated on rotavapor and the residue was diluted with DCM (150 ml). The DCM solution was washed with water, dried over anhydrous sodium sulfate (Na₂SO₄) and evaporated the solvent. The residue was triturated with hexane to give the target indanone 12 as white solid in 97% yield (2.80 g). ¹H NMR (400 MHz, CDCl₃): δ 1.16-0.92 (3H, m); 1.58-1.40 (3H, m); 1.70-1.64 (1H, m); 2.51-2.39 (4H, m); 2.77 (1H, broad s); 2.92-2.87 (2H, m); 3.05-2.09 (1H, m); 3.67 (3H, s); 3.74 (3H, s); 6.66 (1H, s); 6.92 (1H, s). MS (ESI): m/z=290.20 (M+H⁺).

References:

Reviva Pharmaceuticals, Inc. US2008/153878, 2008, A1 Location in patent:Page/Page column 13; 20

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