2-methoxycyclohexan-1-amine

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

Procedure: To methylene chloride (50 ml) are added 4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (45 mmole) and N-methylmorpholine (50 mmole). To the mixture is added dropwise with stirring methyl chloroformate (50 mmole) with keeping the inner temperature at 10°-20° C. by ice-cooling, and thereafter, the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-methoxycyclohexylamine (54 mmole), and the mixture is stirred at the same temperature for 4 hours. After the reaction, water is added to the reaction mixture. The organic layer is separated and washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order, and dried over sodium sulfate. Inorganic materials are filtered off, and the mother liquor is concentrated. The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V) to isolate N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 43%), colorless liquid, nD11 =1.5263. at 10°-20° C. cooling the mixture is stirred at the same temperature for 4 hours is added to the reaction mixture The organic layer is separated washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order dried over sodium sulfate Inorganic materials are filtered off the mother liquor is concentrated The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V)

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

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

Procedure: To methylene chloride (50 ml) are added 4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (45 mmole) and N-methylmorpholine (50 mmole). To the mixture is added dropwise with stirring methyl chloroformate (50 mmole) with keeping the inner temperature at 10°-20° C. by ice-cooling, and thereafter, the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-methoxycyclohexylamine (54 mmole), and the mixture is stirred at the same temperature for 4 hours. After the reaction, water is added to the reaction mixture. The organic layer is separated and washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order, and dried over sodium sulfate. Inorganic materials are filtered off, and the mother liquor is concentrated. The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V) to isolate N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 43%), colorless liquid, nD11 =1.5263. at 10°-20° C. cooling the mixture is stirred at the same temperature for 4 hours is added to the reaction mixture The organic layer is separated washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order dried over sodium sulfate Inorganic materials are filtered off the mother liquor is concentrated The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V)

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

Procedure: To methylene chloride (50 ml) are added 4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (45 mmole) and N-methylmorpholine (50 mmole). To the mixture is added dropwise with stirring methyl chloroformate (50 mmole) with keeping the inner temperature at 10°-20° C. by ice-cooling, and thereafter, the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-methoxycyclohexylamine (54 mmole), and the mixture is stirred at the same temperature for 4 hours. After the reaction, water is added to the reaction mixture. The organic layer is separated and washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order, and dried over sodium sulfate. Inorganic materials are filtered off, and the mother liquor is concentrated. The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V) to isolate N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 43%), colorless liquid, nD11 =1.5263. at 10°-20° C. cooling the mixture is stirred at the same temperature for 4 hours is added to the reaction mixture The organic layer is separated washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order dried over sodium sulfate Inorganic materials are filtered off the mother liquor is concentrated The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V)

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

Procedure: Shake a mixture of o-anisidine (5.0 g, 41 mmol) and rhodium on carbon (5% Rh; 5.0 g) in AcOH (65 mL) under H2 (60 psig) at 60° C. for 6 h. Filter the reaction mixture and rotary, evaporate the filtrate (75° C.). Dissolve this material in CHCl3 (100 mL) and basifiy with satd aq NaHCO3 (50 mL). Dry the organic layer (Na2SO4) and rotary evaporate (40° C.) to yield 1.20 g of 2-methoxy-cyclohexylamine as a yellow oil. Filter the reaction mixture rotary, evaporate the filtrate (75° C.) Dissolve this material in CHCl3 (100 mL) Dry the organic layer (Na2SO4) rotary evaporate (40° C.)

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

Procedure: To methylene chloride (50 ml) are added 4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (45 mmole) and N-methylmorpholine (50 mmole). To the mixture is added dropwise with stirring methyl chloroformate (50 mmole) with keeping the inner temperature at 10°-20° C. by ice-cooling, and thereafter, the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-methoxycyclohexylamine (54 mmole), and the mixture is stirred at the same temperature for 4 hours. After the reaction, water is added to the reaction mixture. The organic layer is separated and washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order, and dried over sodium sulfate. Inorganic materials are filtered off, and the mother liquor is concentrated. The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V) to isolate N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 43%), colorless liquid, nD11 =1.5263. at 10°-20° C. cooling the mixture is stirred at the same temperature for 4 hours is added to the reaction mixture The organic layer is separated washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order dried over sodium sulfate Inorganic materials are filtered off the mother liquor is concentrated The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V)

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

Procedure: To methylene chloride (50 ml) are added 4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (45 mmole) and N-methylmorpholine (50 mmole). To the mixture is added dropwise with stirring methyl chloroformate (50 mmole) with keeping the inner temperature at 10°-20° C. by ice-cooling, and thereafter, the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-methoxycyclohexylamine (54 mmole), and the mixture is stirred at the same temperature for 4 hours. After the reaction, water is added to the reaction mixture. The organic layer is separated and washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order, and dried over sodium sulfate. Inorganic materials are filtered off, and the mother liquor is concentrated. The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V) to isolate N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 43%), colorless liquid, nD11 =1.5263. at 10°-20° C. cooling the mixture is stirred at the same temperature for 4 hours is added to the reaction mixture The organic layer is separated washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order dried over sodium sulfate Inorganic materials are filtered off the mother liquor is concentrated The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V)

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

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

Procedure: To methylene chloride (50 ml) are added 4-(1-methyl-1,2,3,4-tetrazol-5yl)thio-butyric acid (45 mmole) and N-methylmorpholine (50 mmole). To the mixture is added dropwise with stirring methyl chloroformate (50 mmole) with keeping the inner temperature at 10°-20° C. by ice-cooling, and thereafter, the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-methoxycyclohexylamine (54 mmole), and the mixture is stirred at the same temperature for 4 hours. After the reaction, water is added to the reaction mixture. The organic layer is separated and washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order, and dried over sodium sulfate. Inorganic materials are filtered off, and the mother liquor is concentrated. The resulting residue is subjected to column chromatograpy (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V) to isolate N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 43%), colorless liquid, nD11 =1.5263. at 10°-20° C. cooling the mixture is stirred at the same temperature for 4 hours is added to the reaction mixture The organic layer is separated washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order dried over sodium sulfate Inorganic materials are filtered off the mother liquor is concentrated The resulting residue is subjected to column chromatograpy (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V)

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

Procedure: Shake a mixture of o-anisidine (5.0 g, 41 mmol) and rhodium on carbon (5% Rh; 5.0 g) in AcOH (65 mL) under H2 (60 psig) at 60° C. for 6 h. Filter the reaction mixture and rotary evaporate the filtrate (75° C.). Dissolve this material in CHCl3 (100 mL) and basify with satd aq NaHCO3 (50 mL). Dry the organic layer (Na2SO4) and rotary evaporate (40° C.) to yield 1.20 g of 2-methoxy-cyclohexylamine as a yellow oil. Filter the reaction mixture rotary evaporate the filtrate (75° C.) Dissolve this material in CHCl3 (100 mL) Dry the organic layer (Na2SO4) rotary evaporate (40° C.)

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

Procedure: To methylene chloride (50 ml) are added 4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (45 mmole) and N-methylmorpholine (50 mmole). To the mixture is added dropwise with stirring methyl chloroformate (50 mmole) with keeping the inner temperature at 10°-20° C. by ice-cooling, and thereafter, the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-methoxycyclohexylamine (54 mmole), and the mixture is stirred at the same temperature for 4 hours. After the reaction, water is added to the reaction mixture. The organic layer is separated and washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order, and dried over sodium sulfate. Inorganic materials are filtered off, and the mother liquor is concentrated. The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V) to isolate N-(4-methoxycyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 43%), colorless liquid, nD11 =1.5263. at 10°-20° C. cooling the mixture is stirred at the same temperature for 4 hours is added to the reaction mixture The organic layer is separated washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order dried over sodium sulfate Inorganic materials are filtered off the mother liquor is concentrated The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V)

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

Procedure: Shake a mixture of o-anisidine (5.0 g, 41 mmol) and rhodium on carbon (5% Rh; 5.0 g) in AcOH (65 mL) under H2 (60 psig) at 60° C. for 6 h. Filter the reaction mixture and rotary, evaporate the filtrate (75° C.). Dissolve this material in CHCl3 (100 mL) and basifiy with satd aq NaHCO3 (50 mL). Dry the organic layer (Na2SO4) and rotary evaporate (40° C.) to yield 1.20 g of 2-methoxy-cyclohexylamine as a yellow oil. Filter the reaction mixture rotary, evaporate the filtrate (75° C.) Dissolve this material in CHCl3 (100 mL) Dry the organic layer (Na2SO4) rotary evaporate (40° C.)