1-butylpiperidin-4-one

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

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

Procedure: 1-Butyl-4-piperidone oxime is prepared from 1-butyl-4-piperidone and hydroxylamine hydrochloride essentially as described above in Example 38, Scheme C, step b.

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

Procedure: 1-Butyl-4-piperidone is prepared from 4-piperidone and 1-chlorobutane essentially as described above in Example 38, Scheme C, step a.

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

Procedure: 1-Butyl-4-piperidone is prepared from 4-piperidone and 1-chlorobutane essentially as described above in Example 38, Scheme C, step a.

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

Procedure: Beginning with 1.0 gm (4.76 mMol) 5-methanesulfonylamino-1H-indole and 0.96 gm (6.2 mMol) 1-butyl-4-piperidone, 1.4 gm (84.8%) of the title compound were recovered as a yellow powder.

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

Procedure: Beginning with 1.0 gm (4.76 mMol) 5-methanesulfonylamino-1H-indole and 0.96 gm (6.2 mMol) 1-butyl-4-piperidone, 1.4 gm (84.8%) of the title compound were recovered as a yellow powder.

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

Procedure: Beginning with 1.0 gm (4.76 mMol) 5-methanesulfonylamino-1H-indole and 0.96 gm (6.2 mMol) 1-butyl-4-piperidone, 1.4 gm (84.8%) of the title compound were recovered as a yellow powder.

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

Procedure: 1-Butyl-4-piperidone is reacted with dimethylamine gas as described in Example 1, affording 1-butyl-4-dimethylamino-1,2,5,6-tetrahydropyridine with a yield of 77.9%, bp.: 103°-106° C./1.5 kPa. The tetrahydropyridine derivative so obtained is freshly distilled and reacted with acrolein as described in Example 1, to give a light yellow oil with a yield of 44.2%, consisting of 75% of 6α-, and 25% of 6β-dimethylamino-3-butyl-3-azabicyclo[3.3.1]nonan-9-one, bp.: 110°-116° C./7 Pa; nD20 =1.4933.

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

Procedure: 1-Butyl-4-piperidone oxime is prepared from 1-butyl-4-piperidone and hydroxylamine hydrochloride essentially as described above in Example 38, Scheme C, step b.

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

Procedure: 1-Butyl-4-piperidone is prepared from 4-piperidone and 1-chlorobutane essentially as described above in Example 38, Scheme C, step a.

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

Procedure: 1-Butyl-4-piperidone is prepared from 4-piperidone and 1-chlorobutane essentially as described above in Example 38, Scheme C, step a.

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1-butyl-4-piperidone (6.2 g, 40 mmole) and 1-aminopyrrole (3.3 g, 40 mmole) in 100 ml of toluene was stirred at reflux overnight (about 16 hours). The mixture was cooled and then evaporated to an oil, which in turn was dissolved in 75 ml of isopropanol, and 22 ml of ethanol. To the solution was added NaBH4 (3.8 g, 100 mole). The mixture was stirred at 70° C. for 2 hours and then evaporated, stirred with water and extracted with ethyl acetate-ether. The organic extract was washed with water and saturated NaCl solution, dried (anhydrous MgSO4), filtered and evaporated to 13 g of an oil. This oil was purified by high pressure liquid chromatography (silica, 1% diethylamine/ethyl acetate) to give 8.2 g of an oil of 1-(n-butyl)-4-(1H-pyrrol-1-yl)aminopiperidine. at reflux overnight (about 16 hours) The mixture was cooled evaporated to an oil, which in turn was dissolved in 75 ml of isopropanol evaporated stirred with water extracted with ethyl acetate-ether The organic extract was washed with water and saturated NaCl solution dried (anhydrous MgSO4) filtered evaporated to 13 g of an oil This oil was purified by high pressure liquid chromatography (silica, 1% diethylamine/ethyl acetate)