1,2,3,4-tetrahydronaphthalen-1-amine;hydrochloride

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

Procedure: A solution of 18.4 grams (g) of 1,2,3,4-tetrahydro-1-naphthylamine hydrochloride and 8.90 g of sodium dicyanamide in 220 milliliters (ml) of water was heated at 95° C. (steam bath) for 21 hours, after which time a viscous oil had precipitated from the hot solution. The reaction mixture was then cooled and extracted with methylene chloride. The methylene chloride extract was dried over anhydrous sodium sulfate and the sodium sulfate removed by filtration. The methylene chloride was then removed by evaporation in vacuo, leaving the crude product as a pale yellow gum. The gum was crystallized from isopropyl acetate to give an off-white, crystalline solid, melting point (mp) 153.5°-156.5° C. Recrystallization from aqueous ethanol gave 3.87 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)guanidine as a white, crystalline solid, mp 157°-158° C. after which time a viscous oil had precipitated from the hot solution The reaction mixture was then cooled extracted with methylene chloride The methylene chloride extract was dried over anhydrous sodium sulfate the sodium sulfate removed by filtration The methylene chloride was then removed by evaporation in vacuo leaving the crude product as a pale yellow gum The gum was crystallized from isopropyl acetate to give an off-white, crystalline solid point (mp) 153.5°-156.5° C Recrystallization from aqueous ethanol

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

Procedure: A solution of 18.4 grams (g) of 1,2,3,4-tetrahydro-1-naphthylamine hydrochloride and 8.90 g of sodium dicyanamide in 220 milliliters (ml) of water was heated at 95° C. (steam bath) for 21 hours, after which time a viscous oil had precipitated from the hot solution. The reaction mixture was then cooled and extracted with methylene chloride. The methylene chloride extract was dried over anhydrous sodium sulfate and the sodium sulfate removed by filtration. The methylene chloride was then removed by evaporation in vacuo, leaving the crude product as a pale yellow gum. The gum was crystallized from isopropyl acetate to give an off-white, crystalline solid, melting point (mp) 153.5°-156.5° C. Recrystallization from aqueous ethanol gave 3.87 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)guanidine as a white, crystalline solid, mp 157°-158° C. after which time a viscous oil had precipitated from the hot solution The reaction mixture was then cooled extracted with methylene chloride The methylene chloride extract was dried over anhydrous sodium sulfate the sodium sulfate removed by filtration The methylene chloride was then removed by evaporation in vacuo leaving the crude product as a pale yellow gum The gum was crystallized from isopropyl acetate to give an off-white, crystalline solid point (mp) 153.5°-156.5° C Recrystallization from aqueous ethanol

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

Procedure: A solution of 18.4 grams (g) of 1,2,3,4-tetrahydro-1-naphthylamine hydrochloride and 8.90 g of sodium dicyanamide in 220 milliliters (ml) of water was heated at 95° C. (steam bath) for 21 hours, after which time a viscous oil had precipitated from the hot solution. The reaction mixture was then cooled and extracted with methylene chloride. The methylene chloride extract was dried over anhydrous sodium sulfate and the sodium sulfate removed by filtration. The methylene chloride was then removed by evaporation in vacuo, leaving the crude product as a pale yellow gum. The gum was crystallized from isopropyl acetate to give an off-white, crystalline solid, melting point (mp) 153.5°-156.5° C. Recrystallization from aqueous ethanol gave 3.87 g of N'-cyano-N-(1,2,3,4-tetrahydro-1-naphthyl)guanidine as a white, crystalline solid, mp 157°-158° C. after which time a viscous oil had precipitated from the hot solution The reaction mixture was then cooled extracted with methylene chloride The methylene chloride extract was dried over anhydrous sodium sulfate the sodium sulfate removed by filtration The methylene chloride was then removed by evaporation in vacuo leaving the crude product as a pale yellow gum The gum was crystallized from isopropyl acetate to give an off-white, crystalline solid point (mp) 153.5°-156.5° C Recrystallization from aqueous ethanol