1-(cyclopropylmethyl)piperidin-4-one

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

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of bromomethyl cyclopropane (4 mmol) and 4-piperidone hydrate hydrochloride (4 mmol) in acetonitrile (30 mL) was added sodium carbonate (11 mmol). The reaction mixture was stirred 16 h at 85° C. The resulting suspension was filtered and the solid was washed with acetonitrile. The filtrate was concentrated in vacuo and purified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3 to yield 339 mg of the title compound as yellow oil. MS (m/e): 154.2 (MH+, 100%). The resulting suspension was filtered the solid was washed with acetonitrile The filtrate was concentrated in vacuo purified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of bromomethyl cyclopropane (4 mmol) and 4-piperidone hydrate hydrochloride (4 mmol) in acetonitrile (30 mL) was added sodium carbonate (11 mmol). The reaction mixture was stirred 16 h at 85° C. The resulting suspension was filtered and the solid was washed with acetonitrile. The filtrate was concentrated in vacuo and purified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3 to yield 339 mg of the title compound as yellow oil. MS (m/e): 154.2 (MH+, 100%). The resulting suspension was filtered the solid was washed with acetonitrile The filtrate was concentrated in vacuo purified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3

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

Procedure: 1-(Cyclopropylmethyl)-4-piperidone oxime is prepared from 1-(cyclopropylmethyl)-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-(Cyclopropylmethyl)-4-piperidone is prepared from 4-piperidone and (chloromethyl)cyclopropane 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: To a cold (0° C.) solution of 1-cyclopropylmethyl-piperidin-4-one (314 mg, 2 mmol, 1.0 eq.) in ethanol (4 mL) was added sodium borohydride (61 mg, 2 mmol, 0.75 eq.). The reaction mixture was stirred 16 h at room temperature. Water, sodium hydroxide and dichloromethane were added and the reaction mixture was stirred 2 h at room temperature. The aqueous layer was extracted with dichloromethane and the combined organic phases were dried over sodium sulfate, filtered then concentrated to dryness in vacuo to yield 160 mg (50%) of the tide compound as colorless oil, witch was used in the next step without further purification. MS (m/e): 156.3 (MH+, 100%). the reaction mixture was stirred 2 h at room temperature The aqueous layer was extracted with dichloromethane the combined organic phases were dried over sodium sulfate filtered then concentrated to dryness in vacuo

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of (bromomethyl)cyclopropane (500 mg, 4 mmol, 1.0 eq.) and 4-piperidone hydrate hydrochloride (579 mg, 4 mmol, 1.0 eq.) in acetonitrile (30 mL) was added sodium carbonate (1.148 g, 11 mmol, 3. eq.). The reaction mixture was stirred 16 h at 85° C. The resulting suspension was filtered and the solid was washed with acetonitrile. The filtrate was concentrated in vacuo and purified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3 to yield 339 mg (62%) of the tide compound as yellow oil. MS (m/e): 154.2 (MH+, 100%). The resulting suspension was filtered the solid was washed with acetonitrile The filtrate was concentrated in vacuo purified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of (bromomethyl)cyclopropane (500 mg, 4 mmol, 1.0 eq.) and 4-piperidone hydrate hydrochloride (579 mg, 4 mmol, 1.0 eq.) in acetonitrile (30 mL) was added sodium carbonate (1.148 g, 11 mmol, 3. eq.). The reaction mixture was stirred 16 h at 85° C. The resulting suspension was filtered and the solid was washed with acetonitrile. The filtrate was concentrated in vacuo and purified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3 to yield 339 mg (62%) of the tide compound as yellow oil. MS (m/e): 154.2 (MH+, 100%). The resulting suspension was filtered the solid was washed with acetonitrile The filtrate was concentrated in vacuo purified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3

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

Procedure: 1-(Cyclopropylmethyl)-4-piperidone oxime is prepared from 1-(cyclopropylmethyl)-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-(Cyclopropylmethyl)-4-piperidone is prepared from 4-piperidone and (chloromethyl)cyclopropane 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-(Cyclopropylmethyl)-4-piperidone is prepared from 4-piperidone and (chloromethyl)cyclopropane essentially as described above in Example 38, Scheme C, step a.

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of bromomethyl cyclopropane (4 mmol) and 4-piperidone hydrate hydrochloride (4 mmol) in acetonitrile (30 mL) was added sodium carbonate (11 mmol). The reaction mixture was stirred 16 h at 85° C. The resulting suspension was filtered and the solid was washed with acetonitrile. The filtrate was concentrated in vacuo and purified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3 to yield 339 mg of the title compound as yellow oil. MS (m/e): 154.2 (MH+, 100%). The resulting suspension was filtered the solid was washed with acetonitrile The filtrate was concentrated in vacuo purified by column chromatography on silica eluting with DCM/2N NH3 in methanol 97:3