N-benzylprop-2-yn-1-amine

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

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

Procedure: 2 g of dimethyl 5-bromodicarboxylate (from Example 3) and 1.25 g of N-benzylpropargylamine are dissolved in methylene chloride in a flask flushed with argon, and 3.4 ml of triethylamine are added dropwise. The mixture is stirred at room temperature for 15 minutes, 25 mg of ((C6H5)3P)2PdCl2 and 4 mg of CuI are added and the mixture is boiled under reflux for 36 hours. After cooling, the mixture is diluted with methylene chloride and washed with water and sodium chloride solution and the combined organic phases are dried over potassium carbonate. After evaporation, 1.25 g of a dark oil which is hydrogenated without purification (Example 18) remain. flushed with argon, and 3.4 ml of triethylamine are added dropwise 25 mg of ((C6H5)3P)2PdCl2 and 4 mg of CuI are added under reflux for 36 hours After cooling the mixture is diluted with methylene chloride washed with water and sodium chloride solution the combined organic phases are dried over potassium carbonate After evaporation, 1.25 g of a dark oil which is hydrogenated without purification (Example 18)

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

Procedure: 2 g of dimethyl 5-bromodicarboxylate (from Example 3) and 1.25 g of N-benzylpropargylamine are dissolved in methylene chloride in a flask flushed with argon, and 3.4 ml of triethylamine are added dropwise. The mixture is stirred at room temperature for 15 minutes, 25 mg of ((C6H5)3P)2PdCl2 and 4 mg of CuI are added and the mixture is boiled under reflux for 36 hours. After cooling, the mixture is diluted with methylene chloride and washed with water and sodium chloride solution and the combined organic phases are dried over potassium carbonate. After evaporation, 1.25 g of a dark oil which is hydrogenated without purification (Example 18) remain. flushed with argon, and 3.4 ml of triethylamine are added dropwise 25 mg of ((C6H5)3P)2PdCl2 and 4 mg of CuI are added under reflux for 36 hours After cooling the mixture is diluted with methylene chloride washed with water and sodium chloride solution the combined organic phases are dried over potassium carbonate After evaporation, 1.25 g of a dark oil which is hydrogenated without purification (Example 18)

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

Procedure: To a stirred solution of N-benzylprop-2-yn-1-amine (472 mg, 3.25 mmol) and triethylamine (493 mg, 4.88 mmol) in DCM (16 mL), cooled to 0° C. was added pivaloyl chloride (451 mg, 3.74 mmol). After 1 hour the reaction mixture was applied directly to the top of a silica gel column for purification, eluting with a gradient of 60-100% DCM in hexanes to give the title compound. MS: m/z=230 (M+1). After 1 hour the reaction mixture was applied directly to the top of a silica gel column for purification eluting with a gradient of 60-100% DCM in hexanes

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

Procedure: To a stirred solution of N-benzylprop-2-yn-1-amine (472 mg, 3.25 mmol) and triethylamine (493 mg, 4.88 mmol) in DCM (16 mL), cooled to 0° C. was added pivaloyl chloride (451 mg, 3.74 mmol). After 1 hour the reaction mixture was applied directly to the top of a silica gel column for purification, eluting with a gradient of 60-100% DCM in hexanes to give the title compound. MS: m/z=230 (M+1). After 1 hour the reaction mixture was applied directly to the top of a silica gel column for purification eluting with a gradient of 60-100% DCM in hexanes

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

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

Procedure: Upon refluxing 6.36 g. of 1-p-chlorophenoxy-2,3-epoxypropanol with 5 g. of N-benzylpropargylamine in 50 ml. of ethanol and subsequent removal of the solvent as in Example 1, a yellow oil is obtained. Placing this oil on a silica gel column and eluting said column with ethyl acetate produces the pure yellow liquid 1-(N-benzylpropargylamino)-3-p-chlorophenoxy-2-propanol which shows IR and NMR spectra in accordance with its structure and proper analyses for C19H20NO2Cl. Upon refluxing 6.36 g of ethanol and subsequent removal of the solvent as in Example 1 a yellow oil is obtained eluting

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

Procedure: 2 g of dimethyl 5-bromodicarboxylate (from Example 3) and 1.25 g of N-benzylpropargylamine are dissolved in methylene chloride in a flask flushed with argon, and 3.4 ml of triethylamine are added dropwise. The mixture is stirred at room temperature for 15 minutes, 25 mg of ((C6H5)3P)2PdCl2 and 4 mg of CuI are added and the mixture is boiled under reflux for 36 hours. After cooling, the mixture is diluted with methylene chloride and washed with water and sodium chloride solution and the combined organic phases are dried over potassium carbonate. After evaporation, 1.25 g of a dark oil which is hydrogenated without purification (Example 18) remain. flushed with argon, and 3.4 ml of triethylamine are added dropwise 25 mg of ((C6H5)3P)2PdCl2 and 4 mg of CuI are added under reflux for 36 hours After cooling the mixture is diluted with methylene chloride washed with water and sodium chloride solution the combined organic phases are dried over potassium carbonate After evaporation, 1.25 g of a dark oil which is hydrogenated without purification (Example 18)

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

Procedure: To a stirred solution of N-benzylprop-2-yn-1-amine (472 mg, 3.25 mmol) and triethylamine (493 mg, 4.88 mmol) in DCM (16 mL), cooled to 0° C. was added pivaloyl chloride (451 mg, 3.74 mmol). After 1 hour the reaction mixture was applied directly to the top of a silica gel column for purification, eluting with a gradient of 60-100% DCM in hexanes to give the title compound. MS: m/z=230 (M+1). After 1 hour the reaction mixture was applied directly to the top of a silica gel column for purification eluting with a gradient of 60-100% DCM in hexanes