4-(2-aminopropyl)phenol;hydrobromide

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 1-l. flask, flushed with nitrogen and provided with a stirrer, thermometer, two dropping funnels, and a nitrogen inlet tube was placed a solution of 46.4 g. (0.2 moles) of rac. 4-hydroxy-alpha-methylphenethylamine hydrobromide in 100 ml. of water. The flask was cooled in an ice bath, and when the temperature reached 5° C., 40 ml. of acetic anhydride (0.395 moles) and 440 ml. of 2N NaOH were added simultaneously from the two dropping funnels at approximately equivalent rates, maintaining the temperature below 5° C. An oil gradually separated during the addition, and the mixture was stirred for another 4 hours at 5° C., then allowed to come to room temperature overnight. The oil that had solidified to a mass of crystals was recovered by filtration. After washing with water the solid was dried in vacuo over KOH and CaCl2. Yield, 32 g. of mp. 92°-93.5°. An analytical sample was obtained by recrystallization from ethyl acetate-- 30°-60° C. petroleum ether; mp. 97.5° - 99° C. flask, flushed with nitrogen provided with a stirrer The flask was cooled in an ice bath reached 5° C. maintaining the temperature below 5° C An oil gradually separated during the addition to come to room temperature overnight was recovered by filtration After washing with water the solid was dried in vacuo over KOH and CaCl2 Yield

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

Procedure: A mixture of 2.32 g of 4-(2-aminopropyl)phenol hydrobromide, 4.2 g of sodium bicarbonate, 50 ml of water, 100 ml of ethyl acetate and 2.11 g of 4-chlorophenylsulfonyl chloride is stirred at room temperature for 3 hours. After the reaction, the ethyl acetate layer is separated therefrom, dried and evaporated to remove the solvent. 3.25 g of 4-[2-(4-chlorophenyl)sulfonylaminopropyl)phenol are obtained as brown oil. After the reaction the ethyl acetate layer is separated dried evaporated to remove the solvent

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 1-l. flask, flushed with nitrogen and provided with a stirrer, thermometer, two dropping funnels, and a nitrogen inlet tube was placed a solution of 46.4 g. (0.2 moles) of rac. 4-hydroxy-alpha-methylphenethylamine hydrobromide in 100 ml. of water. The flask was cooled in an ice bath, and when the temperature reached 5° C., 40 ml. of acetic anhydride (0.395 moles) and 440 ml. of 2N NaOH were added simultaneously from the two dropping funnels at approximately equivalent rates, maintaining the temperature below 5° C. An oil gradually separated during the addition, and the mixture was stirred for another 4 hours at 5° C., then allowed to come to room temperature overnight. The oil that had solidified to a mass of crystals was recovered by filtration. After washing with water the solid was dried in vacuo over KOH and CaCl2. Yield, 32 g. of mp. 92°-93.5°. An analytical sample was obtained by recrystallization from ethyl acetate-- 30°-60° C. petroleum ether; mp. 97.5° - 99° C. flask, flushed with nitrogen provided with a stirrer The flask was cooled in an ice bath reached 5° C. maintaining the temperature below 5° C An oil gradually separated during the addition to come to room temperature overnight was recovered by filtration After washing with water the solid was dried in vacuo over KOH and CaCl2 Yield