1-methylpiperidine-4-thiol

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:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium methylate (18.1 g) is added in portions to a solution of 1-methylpiperidine-4-thiol (22 g) in anhydrous tetrahydrofuran (200 ml). After one hour, the diethyl acetal of bromoacetaldehyde (30.3 ml) is added. After 4 hours at room temperature, the solution is heated for 2 hours at 40° C. The insoluble material is filtered off and rinsed with THF. The filtrate is concentrated and then distilled under reduced pressure to give 4-[(2,2-diethoxyethyl)thio]-1-methylpiperidine (36 g; b.p.=104°-108° C. under 0.05 atm) in the form of an oil. After 4 hours at room temperature The insoluble material is filtered off rinsed with THF The filtrate is concentrated distilled under reduced pressure

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

Procedure: Sodium methylate (5.9 g) is added in portions to a solution of 1-methylpiperidine-4-thiol (14 g) in anhydrous tetrahydrofuran (100 ml) at room temperature. After 2 hours at this temperature, chloroacetone (8.8 ml) is added dropwise. After 24 hours, the precipitate is filtered off and the filtrate is concentrated and chromatographed on silica gel (eluent: ethyl acetate, then ethanol) to give 1-methyl-4-[(2-oxopropyl)thio]-piperidine (11.5 g) in the form of an oil. the precipitate is filtered off the filtrate is concentrated chromatographed on silica gel (eluent

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

Procedure: The 4-(2,3,4-trimethoxybenzylthio)piperidine used as starting material, the fumarate of which melts at 154° C., was prepared by the hydrolysis, using potassium hydroxide and ethanol, of 4-(2,3,4-trimethoxybenzylthio)-1-ethoxycarbonylpiperidine (oil), which was itself prepared by the action of ClCOOC2H5 in benzene on 4-(2,3,4-trimethoxybenzylthio)-1-methylpiperidine (m.p. of the corresponding fumarate: 130° C.), which was itself prepared by the condensation of 2,3,4-trimethoxybenzyl chloride in ethanol with the sodium salt of 1-methyl-4-mercaptopiperidine, b.p./13 : 70°-72° C. 130° C. 70°-72° C.

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

Procedure: The 4-(2,3,4-trimethoxybenzylthio)piperidine used as starting material, the fumarate of which melts at 154° C., was prepared by the hydrolysis, using potassium hydroxide and ethanol, of 4-(2,3,4-trimethoxybenzylthio)-1-ethoxycarbonylpiperidine (oil), which was itself prepared by the action of ClCOOC2H5 in benzene on 4-(2,3,4-trimethoxybenzylthio)-1-methylpiperidine (m.p. of the corresponding fumarate: 130° C.), which was itself prepared by the condensation of 2,3,4-trimethoxybenzyl chloride in ethanol with the sodium salt of 1-methyl-4-mercaptopiperidine, b.p./13 : 70°-72° C. 130° C. 70°-72° C.

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium methylate (18.1 g) is added in portions to a solution of 1-methylpiperidine-4-thiol (22 g) in anhydrous tetrahydrofuran (200 ml). After one hour, the diethyl acetal of bromoacetaldehyde (30.3 ml) is added. After 4 hours at room temperature, the solution is heated for 2 hours at 40° C. The insoluble material is filtered off and rinsed with THF. The filtrate is concentrated and then distilled under reduced pressure to give 4-[(2,2-diethoxyethyl)thio]-1-methylpiperidine (36 g; b.p.=104°-108° C. under 0.05 atm) in the form of an oil. After 4 hours at room temperature The insoluble material is filtered off rinsed with THF The filtrate is concentrated distilled under reduced pressure

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

Procedure: Sodium methylate (5.9 g) is added in portions to a solution of 1-methylpiperidine-4-thiol (14 g) in anhydrous tetrahydrofuran (100 ml) at room temperature. After 2 hours at this temperature, chloroacetone (8.8 ml) is added dropwise. After 24 hours, the precipitate is filtered off and the filtrate is concentrated and chromatographed on silica gel (eluent: ethyl acetate, then ethanol) to give 1-methyl-4-[(2-oxopropyl)thio]piperidine (11.5 g) in the form of an oil. the precipitate is filtered off the filtrate is concentrated chromatographed on silica gel (eluent

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

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium methylate (18.1 g) is added in portions to a solution of 1-methylpiperidine-4-thiol (22 g) in anhydrous tetrahydrofuran (200 ml). After one hour, the diethyl acetal of bromoacetaldehyde (30.3 ml) is added. After 4 hours at room temperature, the solution is heated for 2 hours at 40° C. The insoluble material is filtered off and rinsed with THF. The filtrate is concentrated and then distilled under reduced pressure to give 4-[(2,2-diethoxyethyl)thio]-1-methylpiperidine (36 g; b.p.=104°-108° C. under 0.05 atm) in the form of an oil. After 4 hours at room temperature The insoluble material is filtered off rinsed with THF The filtrate is concentrated distilled under reduced pressure

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

Procedure: Sodium methylate (5.9 g) is added in portions to a solution of 1-methylpiperidine-4-thiol (14 g) in anhydrous tetrahydrofuran (100 ml) at room temperature. After 2 hours at this temperature, chloroacetone (8.8 ml) is added dropwise. After 24 hours, the precipitate is filtered off and the filtrate is concentrated and chromatographed on silica gel (eluent: ethyl acetate, then ethanol) to give 1-methyl-4-[(2-oxopropyl)thio]piperidine (11.5 g) in the form of an oil. the precipitate is filtered off the filtrate is concentrated chromatographed on silica gel (eluent