4-(dimethylamino)-2,2-diphenylpentanenitrile

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

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

Procedure: Sodium hydride (19.5 g of an 80% dispersion in oil, 0.65 mol) was added to a 1 L 3-neck round bottom flask and triturated twice with hexane (150 mL) to remove the oil). Tetrahydrofuran (THF)(150 mL) was added to the flask followed by a stir bar and the resulting suspension stirred under argon whilst adding a solution of diphenylacetonitrile (58 g, 0.3 mol) in THF (150 mL) dropwise via a dropping funnel over 40 minutes. It became necessary to cool the flask in a cold water bath during the addition due to the exotherm generated. After stirring a further 10 minutes at room temperature the flask was fitted with a reflux condenser and placed in an ice bath. The resulting green suspension was then treated with 2-dimethylaminoisopropyl chloride hydrochloride (54 g, 0.34 mol) portionwise, via an addition funnel, over 15 minutes with stirring. triturated twice with hexane (150 mL) to remove the oil) Tetrahydrofuran (THF)(150 mL) was added to the flask followed by a stir bar to cool the flask in a cold water bath during the addition due to the exotherm After stirring a further 10 minutes at room temperature the flask was fitted with a reflux condenser placed in an ice bath via an addition funnel, over 15 minutes with stirring

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

Procedure: A solution of 1.5M diisobutylaluminum hydride in toluene (7.5 ml) was added to a stirring solution of 4-dimethylamino-2,2-diphenylpentanenitrile (3 g) in THF (7.5 ml), at -78° C. under nitrogen. The resultant mixture was then removed from the dry ice-acetone bath and allowed to warm to room temperature. Stirring was continued at room temperature for 1 day. Saturated ammonium chloride solution was added, and the resultant mixture was extracted with ethyl acetate (3×). The combined extracts were washed with brine and dried (MgSO4). An equal volume of 10% sulfuric acid was added, and the mixture was stirred at room temperature for 3 hours. Water was added, and the aqueous mixture was again extracted with ethyl acetate (3×). The combined extracts were washed with water and dried (MgSO4). Rotary evaporation of the solution gave a crude product which was treated with anhydrous ether. The separated solid material was filtered off, and the filtrate was again rotary-evaporated to yield 1.4 g of 4-dimethylamino-2,2-diphenylpentanal, as a viscous residue which solidified upon standing. The resultant mixture was then removed from the dry ice-acetone bath Saturated ammonium chloride solution was added the resultant mixture was extracted with ethyl acetate (3×) The combined extracts were washed with brine dried (MgSO4) An equal volume of 10% sulfuric acid was added the mixture was stirred at room temperature for 3 hours Water was added the aqueous mixture was again extracted with ethyl acetate (3×) The combined extracts were washed with water dried (MgSO4) Rotary evaporation of the solution gave a crude product which The separated solid material was filtered off the filtrate was again rotary-evaporated

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

Procedure: Sodium hydride (19.5 g of an 80% dispersion in oil, 0.65 mol) was added to a 1 L 3-neck round bottom flask and triturated twice with hexane (150 mL) to remove the oil). Tetrahydrofuran (THF)(150 mL) was added to the flask followed by a stir bar and the resulting suspension stirred under argon whilst adding a solution of diphenylacetonitrile (58 g, 0.3 mol) in THF (150 mL) dropwise via a dropping funnel over 40 minutes. It became necessary to cool the flask in a cold water bath during the addition due to the exotherm generated. After stirring a further 10 minutes at room temperature the flask was fitted with a reflux condenser and placed in an ice bath. The resulting green suspension was then treated with 2-dimethylaminoisopropyl chloride hydrochloride (54 g, 0.34 mol) portionwise, via an addition funnel, over 15 minutes with stirring. triturated twice with hexane (150 mL) to remove the oil) Tetrahydrofuran (THF)(150 mL) was added to the flask followed by a stir bar to cool the flask in a cold water bath during the addition due to the exotherm After stirring a further 10 minutes at room temperature the flask was fitted with a reflux condenser placed in an ice bath via an addition funnel, over 15 minutes with stirring