undecane-1,11-diamine

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

Procedure: m.p. 141.5°-142.5° C., 22.2 g., was prepared as in Example 1 using 24.8 g. of 4-trifluoromethoxybenzoyl chloride in 100 ml. of ethylene dichloride, 9.3 g. of 1,11-undecanediamine, 120 ml. of 10% aqueous potassium hydroxide solution, 400 ml. of ethylene dichloride and recrystallization from acetonitrile. , was prepared as in Example 1 using 24.8 g of ethylene dichloride and recrystallization from acetonitrile

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

Procedure: m.p. 141.5°-142.5° C., 22.2 g., was prepared as in Example 1 using 24.8 g. of 4-trifluoromethoxybenzoyl chloride in 100 ml. of ethylene dichloride, 9.3 g. of 1,11-undecanediamine, 120 ml. of 10% aqueous potassium hydroxide solution, 400 ml. of ethylene dichloride and recrystallization from acetonitrile. , was prepared as in Example 1 using 24.8 g of ethylene dichloride and recrystallization from acetonitrile

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

Procedure: Condensation of 1-pentene oxide and 1,11-undecanediamine affords N,N'-(1,11-undecylene)-bis[2-hydroxypentylamine] (I: R = CH3 (CH2)2, R' = H, X = (CH2)11, Z = H).

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

Procedure: Condensation of 1-pentene oxide and 1,11-undecanediamine affords N,N'-(1,11-undecylene)-bis[2-hydroxypentylamine] (I: R = CH3 (CH2)2, R' = H, X = (CH2)11, Z = H).

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

Procedure: Condensation of 1-pentene oxide and 1,11-undecanediamine affords N,N'-(1,11-undecylene)-bis[2-hydroxypentylamine] (I: R= CH3 (CH2)2, R' = H, X= (CH2)11, Z= H).

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

Procedure: Using a syringe pump, a solution of di-tert-butyl dicarbonate (2.50 g, 11.45 mmol) in methanol (50 mL) was added to a stirred solution of undecane 1,11-diamine (6) (3.00 g, 16.10 mmol) and diisopropylethylamine (2.90 mL, 16.60 mmol) in methanol (200 mL) over 10 h, and the resulting reaction mixture was stirred at rt for 12 h. The reaction was then concentrated to a white solid. Purification by column chromatography (silica gel, 10:90 methanol/dichloromethane, then 20:80 (10% concentrated ammonium hydroxide in methanol)/dichloromethane) afforded the protected amine 7 (2.19 g, 67% yield) as a white solid: 1H NMR (300 MHz, CD3OD) δ 1.30 (br s, 14H), 1.43 (br s, 13H), 2.61 (t, 2H), 3.00 (t, 2H). the resulting reaction mixture The reaction was then concentrated to a white solid Purification by column chromatography (silica gel, 10:90 methanol/dichloromethane

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

Procedure: Condensation of 1-pentene oxide and 1,11-undecanediamine affords N,N'-(1,11-undecylene)-bis[2-hydroxypentylamine] (I: R = CH3 (CH2)2, R' = H, X = (CH2)11, Z = H).

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

Procedure: m.p. 141.5°-142.5° C., 22.2 g., was prepared as in Example 1 using 24.8 g. of 4-trifluoromethoxybenzoyl chloride in 100 ml. of ethylene dichloride, 9.3 g. of 1,11-undecanediamine, 120 ml. of 10% aqueous potassium hydroxide solution, 400 ml. of ethylene dichloride and recrystallization from acetonitrile. , was prepared as in Example 1 using 24.8 g of ethylene dichloride and recrystallization from acetonitrile