2-methyl-1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline

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

Procedure: The autoclave was cooled and the contents were suction filtered. Gas liquid chromatographic analysis of the colorless liquid filtrate on a 6'×1/8" 10% Carbowax 20M column at 200° C. showed that the only product of the reaction was 2-methyl-1,2,3,4-tetrahydroquinoline (96% 2-methyl-1,2,3,4-tetrahydroquinoline and 4% starting material). There were no detectable amounts of 2-methyl-5,6,7,8-tetrahydroquinoline and 2-methyldecahydroquinoline. Gas liquid chromatographic analysis with an external standard showed that the absolute yield of product based on consumed starting material was 100%. The use of cyclohexane as the solvent instead of n-hexadecane gave the same result (97% of 2-methyl-1,2,3,4-tetrahydroquinoline and 3% of 2-methylquinoline). The autoclave was cooled at 200° C. on consumed

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

Procedure: The autoclave was cooled and the contents were suction filtered. Gas liquid chromatographic analysis of the colorless liquid filtrate on a 6'×1/8" 10% Carbowax 20M column at 200° C. showed that the only product of the reaction was 2-methyl-1,2,3,4-tetrahydroquinoline (96% 2-methyl-1,2,3,4-tetrahydroquinoline and 4% starting material). There were no detectable amounts of 2-methyl-5,6,7,8-tetrahydroquinoline and 2-methyldecahydroquinoline. Gas liquid chromatographic analysis with an external standard showed that the absolute yield of product based on consumed starting material was 100%. The use of cyclohexane as the solvent instead of n-hexadecane gave the same result (97% of 2-methyl-1,2,3,4-tetrahydroquinoline and 3% of 2-methylquinoline). The autoclave was cooled at 200° C. on consumed

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

Procedure: N-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared according to the method described below. To a solution 100 gm (0.65 mol) of 2-methyldecahydroquinoline (trans and cis) in 350 ml acetonitrile, 111 gm (0.72 mole) of ethyl iodide was added. The mixture was stirred (using an overhead stirrer) at room temperature for 96 hours. Then, an additional ½ mole equivalent of ethyl iodide was added and the mixture was heated at reflux for 6 hours. The reaction mixture was concentrated on a rotary evaporator at reduced pressure and the obtained solids were rinsed with 500 ml ethyl ether to remove any unreactive amines and excess iodide. The reaction afforded a mixture of two N-ethyl-2-methyl-decahydroquinolinium hydroiodide salts (mono-ethyl derivatives) and a small mixture of the quaternized derivatives. The products were isolated by recrystallization from isopropyl alcohol several times to give the pure trans-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide and the pure cis-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide (see the scheme below). N-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared the mixture was heated at reflux for 6 hours The reaction mixture was concentrated on a rotary evaporator at reduced pressure the obtained solids were rinsed with 500 ml ethyl ether to remove any unreactive amines and excess iodide The reaction afforded a small mixture of the quaternized derivatives

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

Procedure: N-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared according to the method described below. To a solution 100 gm (0.65 mol) of 2-methyldecahydroquinoline (trans and cis) in 350 ml acetonitrile, 111 gm (0.72 mole) of ethyl iodide was added. The mixture was stirred (using an overhead stirrer) at room temperature for 96 hours. Then, an additional ½ mole equivalent of ethyl iodide was added and the mixture was heated at reflux for 6 hours. The reaction mixture was concentrated on a rotary evaporator at reduced pressure and the obtained solids were rinsed with 500 ml ethyl ether to remove any unreactive amines and excess iodide. The reaction afforded a mixture of two N-ethyl-2-methyl-decahydroquinolinium hydroiodide salts (mono-ethyl derivatives) and a small mixture of the quaternized derivatives. The products were isolated by recrystallization from isopropyl alcohol several times to give the pure trans-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide and the pure cis-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide (see the scheme below). N-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared the mixture was heated at reflux for 6 hours The reaction mixture was concentrated on a rotary evaporator at reduced pressure the obtained solids were rinsed with 500 ml ethyl ether to remove any unreactive amines and excess iodide The reaction afforded a small mixture of the quaternized derivatives

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

Procedure: The autoclave was cooled and the contents were suction filtered. Gas liquid chromatographic analysis of the colorless liquid filtrate on a 6'×1/8" 10% Carbowax 20M column at 200° C. showed that the only product of the reaction was 2-methyl-1,2,3,4-tetrahydroquinoline (96% 2-methyl-1,2,3,4-tetrahydroquinoline and 4% starting material). There were no detectable amounts of 2-methyl-5,6,7,8-tetrahydroquinoline and 2-methyldecahydroquinoline. Gas liquid chromatographic analysis with an external standard showed that the absolute yield of product based on consumed starting material was 100%. The use of cyclohexane as the solvent instead of n-hexadecane gave the same result (97% of 2-methyl-1,2,3,4-tetrahydroquinoline and 3% of 2-methylquinoline). The autoclave was cooled at 200° C. on consumed

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

Procedure: N-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared according to the method described below. To a solution 100 gm (0.65 mol) of 2-methyldecahydroquinoline (trans and cis) in 350 ml acetonitrile, 111 gm (0.72 mole) of ethyl iodide was added. The mixture was stirred (using an overhead stirrer) at room temperature for 96 hours. Then, an additional ½ mole equivalent of ethyl iodide was added and the mixture was heated at reflux for 6 hours. The reaction mixture was concentrated on a rotary evaporator at reduced pressure and the obtained solids were rinsed with 500 ml ethyl ether to remove any unreactive amines and excess iodide. The reaction afforded a mixture of two N-ethyl-2-methyl-decahydroquinolinium hydroiodide salts (mono-ethyl derivatives) and a small mixture of the quaternized derivatives. The products were isolated by recrystallization from isopropyl alcohol several times to give the pure trans-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide and the pure cis-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide (see the scheme below). N-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared the mixture was heated at reflux for 6 hours The reaction mixture was concentrated on a rotary evaporator at reduced pressure the obtained solids were rinsed with 500 ml ethyl ether to remove any unreactive amines and excess iodide The reaction afforded a small mixture of the quaternized derivatives

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

Procedure: N-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared according to the method described below. To a solution 100 gm (0.65 mol) of 2-methyldecahydroquinoline (trans and cis) in 350 ml acetonitrile, 111 gm (0.72 mole) of ethyl iodide was added. The mixture was stirred (using an overhead stirrer) at room temperature for 96 hours. Then, an additional ½ mole equivalent of ethyl iodide was added and the mixture was heated at reflux for 6 hours. The reaction mixture was concentrated on a rotary evaporator at reduced pressure and the obtained solids were rinsed with 500 ml ethyl ether to remove any unreactive amines and excess iodide. The reaction afforded a mixture of two N-ethyl-2-methyl-decahydroquinolinium hydroiodide salts (mono-ethyl derivatives) and a small mixture of the quaternized derivatives. The products were isolated by recrystallization from isopropyl alcohol several times to give the pure trans-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide and the pure cis-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide (see the scheme below). N-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared the mixture was heated at reflux for 6 hours The reaction mixture was concentrated on a rotary evaporator at reduced pressure the obtained solids were rinsed with 500 ml ethyl ether to remove any unreactive amines and excess iodide The reaction afforded a small mixture of the quaternized derivatives

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

Procedure: N-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared according to the method described below. To a solution 100 gm (0.65 mol) of 2-methyldecahydroquinoline (trans and cis) in 350 ml acetonitrile, 111 gm (0.72 mole) of ethyl iodide was added. The mixture was stirred (using an overhead stirrer) at room temperature for 96 hours. Then, an additional ½ mole equivalent of ethyl iodide was added and the mixture was heated at reflux for 6 hours. The reaction mixture was concentrated on a rotary evaporator at reduced pressure and the obtained solids were rinsed with 500 ml ethyl ether to remove any unreactive amines and excess iodide. The reaction afforded a mixture of two N-ethyl-2-methyl-decahydroquinolinium hydroiodide salts (mono-ethyl derivatives) and a small mixture of the quaternized derivatives. The products were isolated by recrystallization from isopropyl alcohol several times to give the pure trans-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide and the pure cis-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide (see the scheme below). N-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared the mixture was heated at reflux for 6 hours The reaction mixture was concentrated on a rotary evaporator at reduced pressure the obtained solids were rinsed with 500 ml ethyl ether to remove any unreactive amines and excess iodide The reaction afforded a small mixture of the quaternized derivatives

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

Procedure: A mixture of 15 g decahydro-quinaldine dissolved in 200 ml of diethylether and 4 g of sodium hydroxide in 50 ml of water is reacted while stirring and cooling at -5° to 0° with 10 g of phosgene. An ethereal solution of 1-chlorocarbonyl-2-methyl-decahydro-quinoline is obtained. When an aqueous solution of 8.4 g of sodium ethylmercaptide is added to the ethereal solution at room temperature with stirring, 16 g of an almost colorless oil are obtained. The physical constants of this oil coincide with those of the compound of Example 1.

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

Procedure: A mixture of 15 g decahydro-quinaldine dissolved in 200 ml of diethylether and 4 g of sodium hydroxide in 50 ml of water is reacted while stirring and cooling at -5° to 0° with 10 g of phosgene. An ethereal solution of 1-chlorocarbonyl-2-methyl-decahydro-quinoline is obtained. When an aqueous solution of 8.4 g of sodium ethylmercaptide is added to the ethereal solution at room temperature with stirring, 16 g of an almost colorless oil are obtained. The physical constants of this oil coincide with those of the compound of Example 1.

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

Procedure: N-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared according to the method described below. To a solution 100 gm (0.65 mol) of 2-methyldecahydroquinoline (trans and cis) in 350 ml acetonitrile, 111 gm (0.72 mole) of ethyl iodide was added. The mixture was stirred (using an overhead stirrer) at room temperature for 96 hours. Then, an additional ½ mole equivalent of ethyl iodide was added and the mixture was heated at reflux for 6 hours. The reaction mixture was concentrated on a rotary evaporator at reduced pressure and the obtained solids were rinsed with 500 ml ethyl ether to remove any unreactive amines and excess iodide. The reaction afforded a mixture of two N-ethyl-2-methyl-decahydroquinolinium hydroiodide salts (mono-ethyl derivatives) and a small mixture of the quaternized derivatives. The products were isolated by recrystallization from isopropyl alcohol several times to give the pure trans-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide and the pure cis-fused ring N-ethyl-2-methyl-decahydroquinolinium hydroiodide (see the scheme below). N-Ethyl-2-methyldecahydroquinolinium hydroiodide was prepared the mixture was heated at reflux for 6 hours The reaction mixture was concentrated on a rotary evaporator at reduced pressure the obtained solids were rinsed with 500 ml ethyl ether to remove any unreactive amines and excess iodide The reaction afforded a small mixture of the quaternized derivatives