β-cyclopentylethyl bromide

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

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

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 4-hydroxybenzenesulfonic acid (6.5 grams, 28.2 mmole) and sodium hydroxide (2.2 grams, 55 mmole) in water (15 mL) was mixed with a solution of 2-(bromoethyl)cyclopentane (15.0 grams, 84.7 mmole) in isopropanol (40 mL) and the resulting mixture was heated at reflux for 2 days. The isopropanol was removed by evaporation under vaccuum. The titled compound, 4.7 grams (57%), was collected by filtration washing with isopropanol. the resulting mixture was heated at reflux for 2 days The isopropanol was removed by evaporation under vaccuum The titled compound, 4.7 grams (57%), was collected by filtration washing with isopropanol

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 4-hydroxybenzenesulfonic acid (6.5 grams, 28.2 mmole) and sodium hydroxide (2.2 grams, 55 mmole) in water (15 mL) was mixed with a solution of 2-(bromoethyl)cyclopentane (15.0 grams, 84.7 mmole) in isopropanol (40 mL) and the resulting mixture was heated at reflux for 2 days. The isopropanol was removed by evaporation under vaccuum. The titled compound, 4.7 grams (57%), was collected by filtration washing with isopropanol. the resulting mixture was heated at reflux for 2 days The isopropanol was removed by evaporation under vaccuum The titled compound, 4.7 grams (57%), was collected by filtration washing with isopropanol

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

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

Procedure: 17.7 g (100 mmole) (2-bromoethyl)-cyclopentane, 32.5 g (124 mmole) triphenylphosphine and 100 ml toluene were boiled for 56 hours under reflux. The mixture was stirred overnight at room temperature. The crystals formed were filtered off by suction, washed with ether and dried under vacuum. The yield of compound (53) was 35.6 g (82% theoretical). under reflux The crystals formed were filtered off by suction washed with ether dried under vacuum

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

Procedure: 17.7 g (100 mmole) (2-bromoethyl)-cyclopentane, 32.5 g (124 mmole) triphenylphosphine and 100 ml toluene were boiled for 56 hours under reflux. The mixture was stirred overnight at room temperature. The crystals formed were filtered off by suction, washed with ether and dried under vacuum. The yield of compound (53) was 35.6 g (82% theoretical). under reflux The crystals formed were filtered off by suction washed with ether dried under vacuum

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

Procedure: A solution of 4-hydroxybenzenesulfonic acid (6.5 grams, 28.2 mmole) and sodium hydroxide (2.2 grams, 55 mmole) in water (15 mL) was mixed with a solution of 2-(bromoethyl)cyclopentane (15.0 grams, 84.7 mmole) in isopropanol (40 mL) and the resulting mixture was heated at reflux for 2 days. The isopropanol was removed by evaporation under vacuum. The titled compound, 4.7 grams (57%), was collected by filtration and washed with isopropanol. the resulting mixture was heated at reflux for 2 days The isopropanol was removed by evaporation under vacuum The titled compound, 4.7 grams (57%), was collected by filtration washed with isopropanol

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chlorophenylhydrazine hydrochloride (1.65 g, 9 mmol) was added to a vigorously stirred mixture of tetra-n-butylammonium chloride (0.126 g, 0.45 mmol) in 50% aqueous sodium hydroxide (9 mL) followed by (2-bromo-ethyl)-cyclopentane (1.74 g, 9.9 mmol). The reaction was heated to 60° C. (oil bath temperature) for 8 h. The reaction was cooled, diluted with water (75 mL) and extracted with chloroform (3×30 mL). The combined organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to an orange oil (0.69 g). The oil was subjected to column chromatography (silica gel, eluent: 50% dichloromethane in hexane followed by 70% dichloromethane in hexane) to give a yellow oil (1.17 g, 55%). The reaction was cooled extracted with chloroform (3×30 mL) The combined organic layer was dried (Na2SO4) filtered concentrated under reduced pressure to an orange oil (0.69 g)

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

Procedure: The title compound was prepared by following General Methods 2, 3 and 4 using 4-chlorophenylhydrazine hydrochloride, (2-bromoethyl)cyclopentane, and tetra-n-butylammonium chloride (General Method 2), 1-(4-chlorophenyl)-1-(2-cyclopentylethyl)hydrazine (Example 4) and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3) and 2-(5-chloro-1-(2-cyclopentylethyl)-1H-indol-3-yl)-N-methylethanamine (Example 13), formaldehyde and TFA in acetonitrile (General Method 4).