3-(Benzylamino)propionitrile

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

Procedure: A mixture of β-cyanoethylbenzylamine (92 g.), conc hydrochloric acid (60 ml.), ethanol (120 ml.), paraformaldehyde (30 g.) and acetone (120 ml.) were heated at reflux for 5 hours. The solvent was removed in vacuo and the residue dissolved in water (100 ml.) and washed with ether (2 × 100 ml.). The aqueous solution was made basic with aqueous potassium carbonate and the solution extracted with ether (3 × 100 ml.). The combined extracts were dried and evaporated to give N-benzyl-N-(2-cyanoethyl)-4-aminobutan-2-one (132 g) which was dissolved in dry benzene (1.3 liter) and sodium methoxide (prepared from sodium (13.2 g) was added portionwise. The mixture was refluxed for 5 hours and the cooled solution washed with 2N HCl (4 × 500 ml.). The combined extracts were made basic with potassium carbonate and extracted into methylene chloride (4 × 500 ml.) and the combined extracts dried (MgSO4) and solvent removed in vacuo. The residual oil was distilled to give 1-benzyl-3-cyano-4-methyl-1,2,5,6-tetrahydropyridine as a colourless oil (40 g.) b.p. 136° C/5 × 10-3 mm. Hg. which was converted to the hydrochloride by treating an ethereal solution with dry HCl gas. The resultant solid was recrystallised from methanol-ether giving the hydrochloride of the title compound as colourless needles (35 g.) m.p. 172° C. Found: C, 68.0; H, 7.0; N, 11.3% C14H16N2HCl requires C, 67.6; H, 6.9; N, 11.3%. were heated at reflux for 5 hours The solvent was removed in vacuo the residue dissolved in water (100 ml.) washed with ether (2 × 100 ml.) the solution extracted with ether (3 × 100 ml.) The combined extracts were dried evaporated

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

Procedure: A mixture of β-cyanoethylbenzylamine (92 g.), conc hydrochloric acid (60 ml.), ethanol (120 ml.), paraformaldehyde (30 g.) and acetone (120 ml.) were heated at reflux for 5 hours. The solvent was removed in vacuo and the residue dissolved in water (100 ml.) and washed with ether (2 × 100 ml.). The aqueous solution was made basic with aqueous potassium carbonate and the solution extracted with ether (3 × 100 ml.). The combined extracts were dried and evaporated to give N-benzyl-N-(2-cyanoethyl)-4-aminobutan-2-one (132 g) which was dissolved in dry benzene (1.3 liter) and sodium methoxide (prepared from sodium (13.2 g) was added portionwise. The mixture was refluxed for 5 hours and the cooled solution washed with 2N HCl (4 × 500 ml.). The combined extracts were made basic with potassium carbonate and extracted into methylene chloride (4 × 500 ml.) and the combined extracts dried (MgSO4) and solvent removed in vacuo. The residual oil was distilled to give 1-benzyl-3-cyano-4-methyl-1,2,5,6-tetrahydropyridine as a colourless oil (40 g.) b.p. 136° C/5 × 10-3 mm. Hg. which was converted to the hydrochloride by treating an ethereal solution with dry HCl gas. The resultant solid was recrystallised from methanol-ether giving the hydrochloride of the title compound as colourless needles (35 g.) m.p. 172° C. Found: C, 68.0; H, 7.0; N, 11.3% C14H16N2HCl requires C, 67.6; H, 6.9; N, 11.3%. were heated at reflux for 5 hours The solvent was removed in vacuo the residue dissolved in water (100 ml.) washed with ether (2 × 100 ml.) the solution extracted with ether (3 × 100 ml.) The combined extracts were dried evaporated

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

Procedure: A mixture of β-cyanoethylbenzylamine (92g.), conc hydrochloric acid (60 ml.), ethanol (120 ml.), paraformaldehyde (30 g.) and acetone (120 ml.) were heated at reflux for 5 hours. The solvent was removed in vacuo and the residue dissolved in water (100 ml.) and washed with ether (2 × 100 ml.). The aqueous solution was made basic with aqueous potassium carbonate and the solution extracted with ether (3 × 100 ml.). The combined extracts were dried and evaporated to give N-benzyl-N-(2-cyanoethyl)-4-aminobutan-2-one(132 g) which was dissolved in dry benzene (1.3 liter) and sodium methoxide (prepared from sodium (13.2g) was added portionwise. The mixture was refluxed for 5 hours and the cooled solution washed with 2N HCl (4 × 500 ml.). The combined extracts were made basic with potassium carbonate and extracted into methylene chloride (4 × 500 ml.) and the combined extracts dried (MgSO4) and solvent removed in vacuo. The residual oil was distilled to give 1-benzyl-3-cyano-4-methyl-1,2,5,6-tetrahydropyridine as a colourless oil (40 g.) b.p. 136°C/5 × 10-3 mm. Hg. which was converted to the hydrochloride by treating an ethereal solution with dry HCl gas. The resultant solid was recrystallised from methanol-ether giving the hydrochloride of the title compound as colourless needles (35 g.) m.p. 172°C. Found: C,68.0; H, 7.0; N, 11.3% C14H16N2HCl requires C, 67.6; H, 6.9; N, 11.3%. were heated at reflux for 5 hours The solvent was removed in vacuo the residue dissolved in water (100 ml.) washed with ether (2 × 100 ml.) the solution extracted with ether (3 × 100 ml.) The combined extracts were dried evaporated

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

Procedure: To a solution of 100 mg (0.23 mmol) 17-hydroxywortmannin in 2 mL CH2Cl2 is added 3-benzylamino-propionitrile (73 μL, 0.46 mmol). The reaction mixture is stirred at room temperature for 12 hours and then concentrated in vacuo. The residue is dissolved in EtOAc and precipitated with hexane. The precipitate is washed two times with hexane to give the product as a yellow solid. MS (ESI) m/z 592 (M+H). concentrated in vacuo The residue is dissolved in EtOAc precipitated with hexane The precipitate is washed two times with hexane

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

Procedure: prepared by reaction of [(2-methoxy-phenyl)-(toluene-2-sulfonyl)-amino]-acetic acid with 3-benzylamino-propionitrile

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

Procedure: prepared by reaction of [(4-tert-butyl-benzenesulfonyl)-p-tolyl-amino]-acetic acid with 3-benzylamino-propionitrile

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

Procedure: A solution of 97.5 g of 2-bromo-α-bromoacetophenone in 200 ml of acetone is poured dropwise, at ambient temperature, into a solution of 61.7 g de N-benzyl-2-cyanoethylamine and 67 ml of diisopropylethylamine in 200 ml of acetone. After stirring for 12 hours, the reaction mixture is evaporated, taken up in ether, washed twice with 500 ml of water each time and dried. After evaporating under reduced pressure, 131.9 g of expected product are obtained. the reaction mixture is evaporated washed twice with 500 ml of water each time dried After evaporating under reduced pressure, 131.9 g of expected product are obtained

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

Procedure: A mixture of β-cyanoethylbenzylamine (92 g.), conc hydrochloric acid (60 ml.), ethanol (120 ml.), paraformaldehyde (30 g.) and acetone (120 ml.) were heated at reflux for 5 hours. The solvent was removed in vacuo and the residue dissolved in water (100 ml.) and washed with ether (2 × 100 ml.). The aqueous solution was made basic with aqueous potassium carbonate and the solution extracted with ether (3 × 100 ml.). The combined extracts were dried and evaporated to give N-benzyl-N-(2-cyanoethyl)-4-aminobutan-2-one (132 g) which was dissolved in dry benzene (1.3 liter) and sodium methoxide (prepared from sodium (13.2 g) was added portionwise. The mixture was refluxed for 5 hours and the cooled solution washed with 2N HCl (4 × 500 ml.). The combined extracts were made basic with potassium carbonate and extracted into methylene chloride (4 × 500 ml.) and the combined extracts dried (MgSO4) and solvent removed in vacuo. The residual oil was distilled to give 1-benzyl-3-cyano-4-methyl-1,2,5,6-tetrahydropyridine as a colourless oil (40 g.) b.p. 136° C/5 × 10-3 mm. Hg. which was converted to the hydrochloride by treating an ethereal solution with dry HCl gas. The resultant solid was recrystallised from methanol-ether giving the hydrochloride of the title compound as colourless needles (35 g.) m.p. 172° C. Found: C, 68.0; H, 7.0; N, 11.3% C14H16N2HCl requires C, 67.6; H, 6.9; N, 11.3%. were heated at reflux for 5 hours The solvent was removed in vacuo the residue dissolved in water (100 ml.) washed with ether (2 × 100 ml.) the solution extracted with ether (3 × 100 ml.) The combined extracts were dried evaporated