3-[2-(3-aminopropoxy)ethoxy]propan-1-amine

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

Procedure: 4,7-Dioxadecane-1,10-diamine (32.6 g, 0.185 mole) in acetonitrile (100 mL) was chilled in an ice bath. To this was slowly added dropwise dansyl chloride (5 g, 0.0185 mole) dissolved in acetonitrile (60 mL) over a 20 min. period. Stirring in an ice bath was continued for 1.5 hr. The reaction mixture was poured into water (about 300 mL) and extracted with dichloromethane (2×100 mL). The combined extracts were washed with water and dried to give an oil. The oil was purified by column chromatography (silica gel eluting with acetonitrile containing increasing amounts of ethanol) to provide 4.6 g of N-(10-amino-4,7-dioxadecyl)-5-dimethylaminonapthalene-1-sulfonamide as a viscous oil. extracted with dichloromethane (2×100 mL) The combined extracts were washed with water dried to give an oil The oil was purified by column chromatography (silica gel eluting with acetonitrile containing increasing amounts of ethanol)

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

Procedure: 4,7-Dioxadecane-1,10-diamine (32.6 g, 0.185 mole) in acetonitrile (100 mL) was chilled in an ice bath. To this was slowly added dropwise dansyl chloride (5 g, 0.0185 mole) dissolved in acetonitrile (60 mL) over a 20 min. period. Stirring in an ice bath was continued for 1.5 hr. The reaction mixture was poured into water (about 300 mL) and extracted with dichloromethane (2×100 mL). The combined extracts were washed with water and dried to give an oil. The oil was purified by column chromatography (silica gel eluting with acetonitrile containing increasing amounts of ethanol) to provide 4.6 g of N-(10-amino-4,7-dioxadecyl)-5-dimethylaminonapthalene-1-sulfonamide as a viscous oil. extracted with dichloromethane (2×100 mL) The combined extracts were washed with water dried to give an oil The oil was purified by column chromatography (silica gel eluting with acetonitrile containing increasing amounts of ethanol)

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

Procedure: 1,7-diamino-3,5dioxaheptane; 1,10-diamino-4,7-dioxadecane; 1,10-diamino-4,7-dioxa-5-methyldecane; 1,11-diamino-4,9-dioxaundecane; 1,11-diamino-4,8-dioxa-5-methylundecane; 1,11-diamino-4,8-dioxa- 5,6-dimetyl-7-propyonylundecane; 1,14-diamino-4,7,10-trioxatetradecane, 1,13-diamino-4,7,10-trioxa-5,8-dimethyltridecane; 1,16-diamino-4,7,10,13-tetraoxahexadecane; 1,20-diamino-4,17-dioxaeicosane; and especially 1,12-diamino-4,9-dioxadodecane, 1,14-diamino-4,11-dioxatetradecane, 1,14-diamino-6,6,8(6,8,8)-trimethyl-4,11-dioxatetradecane, and 1,11-diamino-6,6-dimethyl-4,8-dioxaundecane and the compounds specificed in formulas (b) and (c) wherein m is 2 to 14 and k is 7 to 11, respectively.

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

Procedure: 1,7-diamino-3,5dioxaheptane; 1,10-diamino-4,7-dioxadecane; 1,10-diamino-4,7-dioxa-5-methyldecane; 1,11-diamino-4,9-dioxaundecane; 1,11-diamino-4,8-dioxa-5-methylundecane; 1,11-diamino-4,8-dioxa- 5,6-dimetyl-7-propyonylundecane; 1,14-diamino-4,7,10-trioxatetradecane, 1,13-diamino-4,7,10-trioxa-5,8-dimethyltridecane; 1,16-diamino-4,7,10,13-tetraoxahexadecane; 1,20-diamino-4,17-dioxaeicosane; and especially 1,12-diamino-4,9-dioxadodecane, 1,14-diamino-4,11-dioxatetradecane, 1,14-diamino-6,6,8(6,8,8)-trimethyl-4,11-dioxatetradecane, and 1,11-diamino-6,6-dimethyl-4,8-dioxaundecane and the compounds specificed in formulas (b) and (c) wherein m is 2 to 14 and k is 7 to 11, respectively.

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

Procedure: 4,7-Dioxadecane-1,10-diamine (32.6 g, 0.185 mole) in acetonitrile (100 mL) was chilled in an ice bath. To this was slowly added dropwise dansyl chloride (5 g, 0.0185 mole) dissolved in acetonitrile (60 mL) over a 20 min. period. Stirring in an ice bath was continued for 1.5 hr. The reaction mixture was poured into water (about 300 mL) and extracted with dichloromethane (2×100 mL). The combined extracts were washed with water and dried to give an oil. The oil was purified by column chromatography (silica gel eluting with acetonitrile containing increasing amounts of ethanol) to provide 4.6 g of N-(10-amino-4,7-dioxadecyl)-5-dimethylaminonapthalene-1-sulfonamide as a viscous oil. extracted with dichloromethane (2×100 mL) The combined extracts were washed with water dried to give an oil The oil was purified by column chromatography (silica gel eluting with acetonitrile containing increasing amounts of ethanol)

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

Procedure: 4,7-Dioxadecane-1,10-diamine (32.6 g, 0.185 mole) in acetonitrile (100 mL) was chilled in an ice bath. To this was slowly added dropwise dansyl chloride (5 g, 0.0185 mole) dissolved in acetonitrile (60 mL) over a 20 min. period. Stirring in an ice bath was continued for 1.5 hr. The reaction mixture was poured into water (about 300 mL) and extracted with dichloromethane (2×100 mL). The combined extracts were washed with water and dried to give an oil. The oil was purified by column chromatography (silica gel eluting with acetonitrile containing increasing amounts of ethanol) to provide 4.6 g of N-(10-amino-4,7-dioxadecyl)-5-dimethylaminonaphthalene-1-sulfonamide as a viscous oil. extracted with dichloromethane (2×100 mL) The combined extracts were washed with water dried to give an oil The oil was purified by column chromatography (silica gel eluting with acetonitrile containing increasing amounts of ethanol)

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

Procedure: 4,7-Dioxadecane-1,10-diamine (32.6 g, 0.185 mole) in acetonitrile (100 mL) was chilled in an ice bath. To this was slowly added dropwise dansyl chloride (5 g, 0.0185 mole) dissolved in acetonitrile (60 mL) over a 20 min. period. Stirring in an ice bath was continued for 1.5 hr. The reaction mixture was poured into water (about 300 mL) and extracted with dichloromethane (2×100 mL). The combined extracts were washed with water and dried to give an oil. The oil was purified by column chromatography (silica gel eluting with acetonitrile containing increasing amounts of ethanol) to provide 4.6 g of N-(10-amino-4,7-dioxadecyl)-5-dimethylaminonaphthalene-1-sulfonamide as a viscous oil. extracted with dichloromethane (2×100 mL) The combined extracts were washed with water dried to give an oil The oil was purified by column chromatography (silica gel eluting with acetonitrile containing increasing amounts of ethanol)

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

Procedure: 1,7-diamino-3,5dioxaheptane; 1,10-diamino-4,7-dioxadecane; 1,10-diamino-4,7-dioxa-5-methyldecane; 1,11-diamino-4,9-dioxaundecane; 1,11-diamino-4,8-dioxa-5-methylundecane; 1,11-diamino-4,8-dioxa- 5,6-dimetyl-7-propyonylundecane; 1,14-diamino-4,7,10-trioxatetradecane, 1,13-diamino-4,7,10-trioxa-5,8-dimethyltridecane; 1,16-diamino-4,7,10,13-tetraoxahexadecane; 1,20-diamino-4,17-dioxaeicosane; and especially 1,12-diamino-4,9-dioxadodecane, 1,14-diamino-4,11-dioxatetradecane, 1,14-diamino-6,6,8(6,8,8)-trimethyl-4,11-dioxatetradecane, and 1,11-diamino-6,6-dimethyl-4,8-dioxaundecane and the compounds specificed in formulas (b) and (c) wherein m is 2 to 14 and k is 7 to 11, respectively.