1-propoxypropane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of piperidine, 4-(diphenylmethylene) (0.10 mole) and acrylamide (8.95 g, 0.062 mole) in EtOH (50 ml) was refluxed overnight. This reaction mixture was filtered and concentrated. The resulting while solid residue was dissolved in CHCl3, washed with H2O (3×150 ml), dried (Na2SO4) and the solvent removed to give thick yellow oil. Crystallization from CH2Cl2 --i--Pr2O afforded 29.01 g (75%) of 1-piperidinepropanamide, 4-(diphenylmethylene)-; mp 105°-7° C. This reaction mixture was filtered concentrated The resulting while solid residue was dissolved in CHCl3 washed with H2O (3×150 ml) dried (Na2SO4) the solvent removed to give thick yellow oil Crystallization from CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of piperidine, 4-(diphenylmethylene) (0.10 mole) and acrylamide (8.95 g, 0.062 mole) in EtOH (50 ml) was refluxed overnight. This reaction mixture was filtered and concentrated. The resulting while solid residue was dissolved in CHCl3, washed with H2O (3×150 ml), dried (Na2SO4) and the solvent removed to give thick yellow oil. Crystallization from CH2Cl2 --i--Pr2O afforded 29.01 g (75%) of 1-piperidinepropanamide, 4-(diphenylmethylene)-; mp 105°-7° C. This reaction mixture was filtered concentrated The resulting while solid residue was dissolved in CHCl3 washed with H2O (3×150 ml) dried (Na2SO4) the solvent removed to give thick yellow oil Crystallization from CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Air inside a reaction vessel of the same type as the one used in Example 1 was replaced with a nitrogen gas in a satisfactory manner, after which 50 ml of a dipropyl ether (chain ether solvent) solution containing 0.065 mol of ethyl magnesium bromide was charged to the reaction vessel. Meanwhile, 0.060 mol of bromopentafluorobenzene and 20 ml of dipropyl ether (chain ether solvent) were charged to the dropping funnel. Then, the dipropyl ether solution of bromopentafluorobenzene in the dropping funnel was dropped to the reaction vessel over 1 hour at room temperature, and the reaction solution was stirred for 2 hours at room temperature. Consequently, pentafluorophenyl magnesium bromide was obtained in the form of a colorless dipropyl ether solution. The yield of pentafluorophenyl magnesium bromide measured in the same manner as Example 1 was 94.6 mol % based on bromopentafluorobenzene. Air inside a reaction vessel of the same type as the one used in Example 1 was charged to the reaction vessel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Donepezil (3.79 g, dissolved in 20 ml of ethyl acetate) is slowly added to a solution of maleic acid (0.58 g) in absolute ethanol (5 ml) with stirring at room temperature followed by adding 10 ml of dipropyl ether. The solid precipitated is filtered and dried at 55° C. under vacuum to give the title compound. Melting point: 127.8° C. The solid precipitated is filtered dried at 55° C. under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Maleic acid (1.161 g, dissolved in 10 ml of 2-propanol) is slowly added to a solution of Donepezil (3.79 g) in ethyl acetate (20 ml) with stirring at room temperature followed by adding 10 ml of dipropyl ether. The solid precipitated is filtered and dried at 55° C. under vacuum to give the title compound. Melting point: 126.8° C. The solid precipitated is filtered dried at 55° C. under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Maleic acid (1.161 g, dissolved in 10 ml of absolute ethanol) is slowly added to a solution of Donepezil (3.79 g) in ethyl acetate (20 ml) with stirring at room temperature followed by adding 10 ml of dipropyl ether. The solid precipitated is filtered and dried at 55° C. under vacuum to give the title compound. Melting point: 132.2° C. The solid precipitated is filtered dried at 55° C. under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methanesulfonic acid (1.3 ml, dissolved in 11 ml of absolute ethanol) is slowly added to a solution of Donepezil (3.79 g) in absolute ethanol (38 ml) with stirring at room temperature, and 50 ml of dipropyl ether is added. The solid precipitated is filtered and dried at 55° C. under vacuum to give the title compound. Melting point: 180.3° C. The solid precipitated is filtered dried at 55° C. under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Homogenous catalysts have a distinct advantage in that the application of mechanistic understanding can allow rational tuning of catalyst structure and reaction conditions to optimize activity, selectivity and lifetimes. Schlaf and coworkers have explored the reduction of terminal vicinal diols to n-alcohols using homogeneous Ru ionic hydrogenation catalysts and through these studies have provided insight into various factors that control deoxygenation selectivity. The use of diol models, which are less reactive than their polyol analogs, enabled kinetic analysis and more thorough characterization of product profiles. The most selective of the Ru hydrogenation catalysts was [Cp*Ru(CO)2(H2)][OTf], which achieved a 54% yield of 1-propanol in sulfolane solvent at 110° C. and 710 psi H2 using trifluoromethanesulfonic acid (HOTf) as the catalyst for the initial dehydration step. In addition to the 1-propanol hydrogenation product, the formation of several ether condensation products was observed, including significant yields of propylene glycol propyl ether (11%) and di-n-propyl ether (15%). The overall selectivity for reduction of the secondary hydroxyl group is 99%. The high regioselectivity of the ruthenium catalyst was impressive, but the catalyst is deactivated by water, which is a byproduct of the reaction. The active Ru dihydrogen complex is deprotonated by water to yield an inactive dimer. This catalyst decomposition makes it impractical for use with inherently wet glycerol from biodiesel production. Several ruthenium containing ionic hydrogenation catalysts with N-donor ligands have demonstrated greater solubility and stability in aqueous solution, however significant thermal decomposition and/or reduced selectivities were observed. at 110° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of piperidine, 4-(diphenylmethylene) (0.10 mole) and acrylamide (8.95 g, 0.062 mole) in EtOH (50 ml) was refluxed overnight. This reaction mixture was filtered and concentrated. The resulting while solid residue was dissolved in CHCl3, washed with H2O (3×150 ml), dried (Na2SO4) and the solvent removed to give thick yellow oil. Crystallization from CH2Cl2 --i--Pr2O afforded 29.01 g (75%) of 1-piperidinepropanamide, 4-(diphenylmethylene)-; mp 105°-7° C. This reaction mixture was filtered concentrated The resulting while solid residue was dissolved in CHCl3 washed with H2O (3×150 ml) dried (Na2SO4) the solvent removed to give thick yellow oil Crystallization from CH2Cl2