N'-(3-aminopropyl)propane-1,3-diamine

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

Procedure: Also prepared by this method are 1-[1,3-di-(2-norbornyl)-2-propyl]1,5,9-triazanonane trihydrochloride from 1,3-di-(2-norbornyl)-2-propanone and 3,3'-iminobispropylamine; 1-[1,7-di-(2-norbornyl)-4-heptyl]-1,5,9-triazanonane trihydrochloride from 1,7-di-(2-norbornyl)-4-heptanone and 3,3'-iminobispropylamine and 1-[2,6-di-(2-norbornyl)-4-heptyl]-1,5,9-triazanonane trihydrochloride from 2,6-di-(2-norbornyl)-4-heptanone and 3,3'-iminobispropylamine. Also prepared by this method

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

Procedure: To a stirred solution of p-toluenesulfonyl chloride (240 g, 1.26 mole) in pyridine (600 ml) at 0° C. was added a solution of 1,5,9-triazanonane (50.0 g, 0.381 mole) in pyridine (100 ml) under a dry nitrogen atmosphere, maintaining the temperature ≤60° C. The addition required 15 minutes. The solvent was removed in vacuo and the resulting yellow oil was dissolved in ethyl acetate (1 l) and H2O (500 ml). The ethyl acetate layer was separated, washed with 0.1N HCl, H2O and saturated NaCl solution and dried (MgSO4). The solution was decolorized with silica gel and the solvent was removed in vacuo to give 133 g (59% yield) of the crude product as a glassy solid: 1H NMR (CDCl3) δ 1.71 (quint, J=6.6 Hz, 4 H), 2.42 (s, 6 H), 2.43 (s, 3 H), 2.96 (quart, J=6.4 Hz, 4 H), 3.11 (t, J=6.8 Hz, 4 H), 5.12 (t, J=6.6 Hz, 2 H), 7.30 (m, 6 H), 7.63 (m, 2 H), 7.73 (m, 4 H). maintaining the temperature ≤60° C The addition required 15 minutes The solvent was removed in vacuo the resulting yellow oil was dissolved in ethyl acetate (1 l) The ethyl acetate layer was separated washed with 0.1N HCl, H2O and saturated NaCl solution dried (MgSO4) the solvent was removed in vacuo

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

Procedure: In still another specific exemplary embodiment, as shown in Scheme 3 and Example 2 below, a guanidine carbonate salt (1) is dissolved in water and reacted with hydrochloric acid, followed by addition of dipropylene triamine (2). The resulting solution is warmed to reflux and stirred for 4-6 hours to yield the chloride salt of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (4) in water, as shown below: The resulting solution is warmed to reflux

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

Procedure: To a stirred solution of p-toluenesulfonyl chloride (240 g, 1.26 mole) in pyridine (600 ml) at 0° C. was added a solution of 1,5,9-triazanonane (50.0 g, 0.381 mole) in pyridine (100 ml) under a dry nitrogen atmosphere, maintaining the temperature ≤60° C. The addition required 15 minutes. The solvent was removed in vacuo and the resulting yellow oil was dissolved in ethyl acetate (1 l) and H2O (500 ml). The ethyl acetate layer was separated, washed with 0.1N HCl, H2O and saturated NaCl solution and dried (MgSO4). The solution was decolorized with silica gel and the solvent was removed in vacuo to give 133 g (59% yield) of the crude product as a glassy solid: 1H NMR (CDCl3) δ1.71 (quint, J=6.6 Hz, 4 H), 2.42 (s, 6 H), 2.43 (s, 3 H), 2.96 (quart, J=6.4 Hz, 4 H), 3.11 (t, J=6.8 Hz, 4 H), 5.12 (t, J=6.6 Hz, 2 H), 7.30 (m, 6 H), 7.63 (m, 2 H), 7.73 (m, 4 H). maintaining the temperature ≤60° C The addition required 15 minutes The solvent was removed in vacuo the resulting yellow oil was dissolved in ethyl acetate (1 l) The ethyl acetate layer was separated washed with 0.1N HCl, H2O and saturated NaCl solution dried (MgSO4) the solvent was removed in vacuo

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

Procedure: A solution of 33 g of tert-butyl dicarbonate in 200 ml of methylene chloride was added at 5° C. to a solution of 39.3 g of 3,3'-diaminodipropylamine in 300 ml of methylene chloride and after stirringf or 16 hours at 20° C., water was added, followed by decanting and evaporation to dryness. The residue was chromatographed on silica (eluant; methanol-ammonia (98-2)) to obtain 15.5 g of the expected product which was used as is for the next step. by decanting evaporation to dryness The residue was chromatographed on silica (eluant; methanol-ammonia (98-2))

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

Procedure: Also prepared by this method in an analogous manner regarding molar quantities and reaction conditions are 1-[1,3-di-(bicyclo[2.2.2]oct-2-yl)-2-propyl]-1,5,9-triazanonane trihydrochloride from 1,3-di-(bicyclo[2.2.2]oct-2-yl)-2-propanone and 3,3'-iminobispropylamine; 1-[1,3-di-(bicyclo[2.2.2]oct-2-yl)-2-propyl]-1,4,7,10-tetraazadecane tetrahydrochloride from 1,3-di-(bicyclo[2.2.2]oct-2-yl)-2-propanone and triethylenetetramine; 1-[1,7-di-(bicyclo[2.2.2-oct-2-yl)-4-heptyl]-1,5,9-triazanonane trihydrochloride from 1,7-di-(bicyclo[2.2.2]oct-2-yl)-4-heptanone and 3,3'-iminobispropylamine and 1-[2,6-di-(bicyclo[2.2.2]oct-2-yl)-4-heptyl]-1,5,9-triazanonane trihydrochloride from 2,6-di-(bicyclo[2.2.2]oct-2-yl)-4-heptanone and 3,3'-iminobispropylamine. Also prepared by this method in an analogous manner quantities and reaction conditions

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

Procedure: Also prepared by this method in an analogous manner regarding molar quantities and reaction conditions are 1-[1,3-di-(2-norbornyl)-2-propyl]-1,5,9-triazanonane trihydrochloride from 1,3-di-(2-norbornyl)-2-propanone and 3,3'-iminobispropylamine; 1-[1,3-di-2-norbornyl-2-propyl]-1,4,7,10-tetraazadecane tetrahydrochloride from 1,3-di-(2-norbornyl)-2-propanone and triethylenetetramine; 1-[1,7-di-(2-norbornyl)-4-heptyl]-1,5,9-triazanonane trihydrochloride from 1,7-di-(2-norbornyl)-4-heptanone and 3,3'-iminobispropylamine and 1-[2,6-di-(2-norbornyl)-4-heptyl]-1,5,9-triazanonane trihydrochloride from 2,6-di-(2-norbornyl)-4-heptanone and 3,3'-iminobispropylamine. Also prepared by this method in an analogous manner quantities and reaction conditions

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

Procedure: Also prepared by this method in an analogous manner regarding molar quantities and reaction conditions are 1-[1,3-di-(2-norbornyl)-2-propyl]-1,5,9-triazanonane trihydrochloride from 1,3-di-(2-norbornyl)-2-propanone and 3,3'-iminobispropylamine; 1-[1,3-di-2-norbornyl-2-propyl]-1,4,7,10-tetraazadecane tetrahydrochloride from 1,3-di-(2-norbornyl)-2-propanone and triethylenetetramine; 1-[1,7-di-(2-norbornyl)-4-heptyl]-1,5,9-triazanonane trihydrochloride from 1,7-di-(2-norbornyl)-4-heptanone and 3,3'-iminobispropylamine and 1-[2,6-di-(2-norbornyl)-4-heptyl]-1,5,9-triazanonane trihydrochloride from 2,6-di-(2-norbornyl)-4-heptanone and 3,3'-iminobispropylamine. Also prepared by this method in an analogous manner quantities and reaction conditions

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

Procedure: N,N-Bis-[3-(3,4-dihydro-1,3-dioxo-2(1H)-isoquinolyl)-propyl]-amine was prepared analogous to Example 30 from 2.44 gm of isochroman-1,3-dione and N,N-bis-(3-amino-propyl)-amine. The hydrochloride was precipitated from acetone with ethereal hydrochloric acid. M.p. of the hydrochloride: 135° -140° C; yield: 0.17 gm (2.5% of the theory). The hydrochloride was precipitated from acetone with ethereal hydrochloric acid 135° -140° C

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

Procedure: Also prepared by this method are 1-[1,3-di-(2-norbornyl)-2-propyl]1,5,9-triazanonane trihydrochloride from 1,3-di-(2-norbornyl)-2-propanone and 3,3'-iminobispropylamine; 1-[1,7-di-(2-norbornyl)-4-heptyl]-1,5,9-triazanonane trihydrochloride from 1,7-di-(2-norbornyl)-4-heptanone and 3,3'-iminobispropylamine and 1-[2,6-di-(2-norbornyl)-4-heptyl]-1,5,9-triazanonane trihydrochloride from 2,6-di-(2-norbornyl)-4-heptanone and 3,3'-iminobispropylamine. Also prepared by this method

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

Procedure: Also prepared by this method are 1-[1,3-di-(2-norbornyl)-2-propyl]1,5,9-triazanonane trihydrochloride from 1,3-di-(2-norbornyl)-2-propanone and 3,3'-iminobispropylamine; 1-[1,7-di-(2-norbornyl)-4-heptyl]-1,5,9-triazanonane trihydrochloride from 1,7-di-(2-norbornyl)-4-heptanone and 3,3'-iminobispropylamine and 1-[2,6-di-(2-norbornyl)-4-heptyl]-1,5,9-triazanonane trihydrochloride from 2,6-di-(2-norbornyl)-4-heptanone and 3,3'-iminobispropylamine. Also prepared by this method

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

Procedure: To a stirred solution of p-toluenesulfonyl chloride (240 g, 1.26 mole) in pyridine (600 ml) at 0° C. was added a solution of 1,5,9-triazanonane (50.0 g, 0.381 mole) in pyridine (100 ml) under a dry nitrogen atmosphere, maintaining the temperature ≤60° C. The addition required 15 minutes. The solvent was removed in vacuo and the resulting yellow oil was dissolved in ethyl acetate (1 l) and H2O (500 ml). The ethyl acetate layer was separated, washed with 0.1N HCl, H2O and saturated NaCl solution and dried (MgSO4). The solution was decolorized with silica gel and the solvent was removed in vacuo to give 133 g (59% yield) of the crude product as a glassy solid: 1H NMR (CDCl3) δ 1.71 (quint, J=6.6 Hz, 4 H), 2.42 (s, 6 H), 2.43 (s, 3 H), 2.96 (quart, J=6.4 Hz, 4 H), 3.11 (t, J=6.8 Hz, 4 H), 5.12 (t, J=6.6 Hz, 2 H), 7.30 (m, 6 H), 7.63 (m, 2 H), 7.73 (m, 4 H). maintaining the temperature ≤60° C The addition required 15 minutes The solvent was removed in vacuo the resulting yellow oil was dissolved in ethyl acetate (1 l) The ethyl acetate layer was separated washed with 0.1N HCl, H2O and saturated NaCl solution dried (MgSO4) the solvent was removed in vacuo