3-(3-hydroxypropylamino)propanenitrile

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

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

Procedure: A solution of 75 g. (1 mole) of 3-aminopropanol is stirred while 54 g. (1 mole) of acrylonitrile is added dropwise. After being allowed to stand at room temperature for several hours and preferably overnight, the reaction mixture is concentrated under reduced pressure at 50° yielding 3-(2-cyanoethyl)aminopropanol. the reaction mixture is concentrated under reduced pressure at 50°

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

Procedure: In a third alternative synthesis of monomer I, 3-aminopropanol is added to acrylonitrile yielding 3-(2-cyanoethyl)aminopropanol, which in turn is converted in two steps to 3-[N-(2-cyanoethyl)-N-formylamino]propanol. The nitrile function of the latter is catalytically reduced to a primary amine function which in turn is exhaustively alkylated with a methyl halide to yield a 3-[N'-formyl-N'-(3-hydroxypropyl)amino]-N,N,N-trimethyl-1-propanaminium halide. Reduction of the formyl moiety in the latter to a methyl function is accomplished by treating this intermediate with a formic acid-formalin mixture at 60° C.-100° C. for 10-24 hours, followed by acidification with the appropriate aqueous hydrogen halide and concentration to dryness yielding a 3-[N'-(3-hydroxypropyl)-N'-methylamino] -N,N,N-trimethyl-1-propanaminium halide hydrohalide. Conversion of this intermediate to 3-[N'-(3-halopropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium halide hydrohalide is accomplished as described in our preferred synthesis of monomer I above, and anion exchange, if desired, is effected by any of the heretofore described procedures.

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

Procedure: A solution of 127.7 g. of 3-(2-cyanoethyl)aminopropanol in 1 liter of 99% formic acid is heated at 85° for 15 hours. The reaction mixture is concentrated under reduced pressure at 80° and the residue is taken up in 60 ml. of methylene chloride-ethyl acetate (1:1). A 1500 g. silica gel G column packed in methylene chloride-ethyl acetate is prepared, and the product is purified by adsorption on silica gel G followed by elution using the 1:1 methylene chloride-ethyl acetate system. Concentration of the combined eluates yields the formate ester of 3-[N-(2-cyanoethyl)-N-formylamino]propanol. The reaction mixture is concentrated under reduced pressure at 80° is prepared the product is purified by adsorption on silica gel G followed by elution

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

Procedure: A solution of 127.7 g. of 3-(2-cyanoethyl)aminopropanol in 1 liter of 99% formic acid is heated at 85° for 15 hours. The reaction mixture is concentrated under reduced pressure at 80° and the residue is taken up in 60 ml. of methylene chloride-ethyl acetate (1:1). A 1500 g. silica gel G column packed in methylene chloride-ethyl acetate is prepared, and the product is purified by adsorption on silica gel G followed by elution using the 1:1 methylene chloride-ethyl acetate system. Concentration of the combined eluates yields the formate ester of 3-[N-(2-cyanoethyl)-N-formylamino]propanol. The reaction mixture is concentrated under reduced pressure at 80° is prepared the product is purified by adsorption on silica gel G followed by elution

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

Procedure: A solution of 75 g. (1 mole) of 3-aminopropanol is stirred while 54 g. (1 mole) of acrylonitrile is added dropwise. After being allowed to stand at room temperature for several hours and preferably overnight, the reaction mixture is concentrated under reduced pressure at 50° yielding 3-(2-cyanoethyl)aminopropanol. the reaction mixture is concentrated under reduced pressure at 50°

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

Procedure: A solution of 75 g. (1 mole) of 3-aminopropanol is stirred while 54 g. (1 mole) of acrylonitrile is added dropwise. After being allowed to stand at room temperature for several hours and preferably overnight, the reaction mixture is concentrated under reduced pressure at 50° yielding 3-(2-cyanoethyl)aminopropanol. the reaction mixture is concentrated under reduced pressure at 50°

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

Procedure: In a third alternative synthesis of monomer I, 3-aminopropanol is added to acrylonitrile yielding 3-(2-cyanoethyl)aminopropanol, which in turn is converted in two steps to 3-[N-(2-cyanoethyl)-N-formylamino]propanol. The nitrile function of the latter is catalytically reduced to a primary amine function which in turn is exhaustively alkylated with a methyl halide to yield a 3-[N'-formyl-N'-(3-hydroxypropyl)amino]-N,N,N-trimethyl-1-propanaminium halide. Reduction of the formyl moiety in the latter to a methyl function is accomplished by treating this intermediate with a formic acid-formalin mixture at 60° C.-100° C. for 10-24 hours, followed by acidification with the appropriate aqueous hydrogen halide and concentration to dryness yielding a 3-[N'-(3-hydroxypropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium halide hydrohalide. Conversion of this intermediate to 3-[N'-(3-halopropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium halide hydrohalide is accomplished as described in our preferred synthesis of monomer I above, and anion exchange, if desired, is effected by any of the heretofore described procedures.

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

Procedure: In a third alternative synthesis of monomer I, 3-aminopropanol is added to acrylonitrile yielding 3-(2-cyanoethyl)aminopropanol, which in turn is converted in two steps to 3-[N-(2-cyanoethyl)-N-formylamino]propanol. The nitrile function of the latter is catalytically reduced to a primary amine function which in turn is exhaustively alkylated with a methyl halide to yield a 3-[N'-formyl-N'-(3-hydroxypropyl)amino]-N,N,N-trimethyl-1-propanaminium halide. Reduction of the formyl moiety in the latter to a methyl function is accomplished by treating this intermediate with a formic acid-formalin mixture at 60° C.-100° C. for 10-24 hours, followed by acidification with the appropriate aqueous hydrogen halide and concentration to dryness yielding a 3-[N'-(3-hydroxypropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium halide hydrohalide. Conversion of this intermediate to 3-[N'-(3-halopropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium halide hydrohalide is accomplished as described in our preferred synthesis of monomer I above, and anion exchange, if desired, is effected by any of the heretofore described procedures.

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

Procedure: 75 grams (1 mole) of 3-amino-propanol were treated with 53 grams (1 mole) of acrylonitrile within one hour at 25° C. The mixture was allowed to react further for 1 hour at 40° C. The thus obtained reaction product (128 grams) was directly reacted further with formaldehyde/hydrocyanic acid or formaldehyde/alkali salt of hydrocyanic acid in the presence of alkali hydrogen sulfite. to react further for 1 hour at 40° C

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

Procedure: 75 grams (1 mole) of 3-amino-propanol were treated with 53 grams (1 mole) of acrylonitrile within one hour at 25° C. The mixture was allowed to react further for 1 hour at 40° C. The thus obtained reaction product (128 grams) was directly reacted further with formaldehyde/hydrocyanic acid or formaldehyde/alkali salt of hydrocyanic acid in the presence of alkali hydrogen sulfite. to react further for 1 hour at 40° C

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

Procedure: A solution of 75 g. (1 mole) of 3-aminopropanol is stirred while 54 g. (1 mole) of acrylonitrile is added dropwise. After being allowed to stand at room temperature for several hours and preferably overnight, the reaction mixture is concentrated under reduced pressure at 50° yielding 3-(2-cyanoethyl)aminopropanol. the reaction mixture is concentrated under reduced pressure at 50°