N,6-dimethylhept-5-en-2-amine

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

Procedure: Mucic acid (628 mg, 3.0 mmol) was suspended in distilled water (40 mL) at room temperature (RT). Isometheptene-isomer-2 (3.04 g, 21.5 mmol) was dissolved in Et2O (57 mL) and added dropwise via addition funnel to the mucic acid at RT while stirring to give dissolution of the mucic acid suspension. The biphasic solution was stirred at RT for 16 h, the aqueous layer was separated, extracted with toluene (5×80 mL) (the final extraction with toluene was stood for 30 min before the aqueous layer was separated), then the aqueous layer was evaporated in vacuo (1 mm Hg) at 35°-40° C. to give a white solid which was dissolved in MeOH (8 mL) by gently heating to give a solution. CH3CN (80 mL) was added slowly dropwise via addition funnel at RT to the stirred MeOH solution to give a suspension which was stirred at RT for about 30 min. The solids were filtered, washed with CH3CN thrice, air-dried, then dried in vacuo (0.1 mm Hg) at RT for 16 h to give the titled compound as a white (1.390 mg, 70%). The molar ratio of Isometheptene to mucic acid in the salt was 2:1, based on the NMR spectrum: 1H NMR (500 MHz, in D2O), 1H NNMR in CDCl3: 5.16 ppm 1 Ht (J=6.8 Hz), 4.25 ppm 1 Hs, 3.95 ppm 1 Hs, 3.2 ppm 1 Hm, 2.66 ppm 3 Hs, 2.09 ppm 2 Hm, 1.75 ppm 1 Hm, 1.69 ppm 3 Hs, 1.62 ppm 3 Hs, 1.58 ppm 1 Hm, 1.29 ppm 3 Hd (J=7 Hz). MS: mass calc for C9H19N, 141.15. Found: 142.4 (M+H). (RT) to give The biphasic solution was stirred at RT for 16 h the aqueous layer was separated extracted with toluene (5×80 mL) (the final extraction with toluene was separated), then the aqueous layer was evaporated in vacuo (1 mm Hg) at 35°-40° C. to give a white solid which by gently heating to give a solution to give a suspension which was stirred at RT for about 30 min The solids were filtered washed with CH3CN thrice air-dried dried in vacuo (0.1 mm Hg) at RT for 16 h

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

Procedure: Mucic acid (628 mg, 3.0 mmol) was suspended in distilled water (40 mL) at RT. Isometheptene-isomer-2 (3.04 g, 21.5 mmol) was dissolved in Et2O (57 mL) and added dropwise via addition funnel to the mucic acid at RT while stirring to give dissolution of the mucic acid suspension. The biphasic solution was stirred at RT for 16 h, the aqueous layer was separated, extracted with toluene (5×80 mL) (the final extraction with toluene was stood for 30 min before the aqueous layer was separated), then the aqueous layer was evaporated in vacuo (1 mm Hg) at 35°-40° C. to give a white solid which was dissolved in MeOH (8 mL) by gently heating to give a solution. CH3CN (80 mL) was added slowly dropwise via addition funnel at RT to the stirred MeOH solution to give a suspension which was stirred at RT for about 30 min. The solids were filtered, washed with CH3CN thrice, air-dried, then dried in vacuo (0.1 mm Hg) at RT for 16 h to give the titled compound as a white (1.390 mg, 70%). The molar ratio of Isometheptene to mucic acid in the salt was 2:1, based on the NMR spectrum: 1H NMR (500 MHz, in D2O), 1H NNMR in CDCl3: 5.16 ppm 1 Ht (J=6.8 Hz), 4.25 ppm 1 Hs, 3.95 ppm 1 Hs, 3.2 ppm 1 Hm, 2.66 ppm 3 Hs, 2.09 ppm 2 Hm, 1.75 ppm 1 Hm, 1.69 ppm 3 Hs, 1.62 ppm 3 Hs, 1.58 ppm 1 Hm, 1.29 ppm 3 Hd (J=7 Hz). MS: mass calc for C9H19N, 141.15. Found: 142.4 (M+H). to give The biphasic solution was stirred at RT for 16 h the aqueous layer was separated extracted with toluene (5×80 mL) (the final extraction with toluene was separated), then the aqueous layer was evaporated in vacuo (1 mm Hg) at 35°-40° C. to give a white solid which by gently heating to give a solution to give a suspension which was stirred at RT for about 30 min The solids were filtered washed with CH3CN thrice air-dried dried in vacuo (0.1 mm Hg) at RT for 16 h

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

Procedure: Mucic acid (840 mg, 4.0 mmol) was suspended in distilled water (40 mL) at RT. Isometheptene-isomer-1 (1.356 g, 9.6 mmol) was dissolved in Et2O (19 mL) and added dropwise via addition funnel to the mucic acid at RT while stirring to give dissolution of the mucic acid suspension. The biphasic solution was stirred at RT for 16 h, the aqueous layer was separated, extracted with toluene (5×80 mL) (the final extraction with toluene was stood for 30 min before the aqueous layer was separated), then the aqueous layer was evaporated in vacuo (1 mm Hg) at 35°-40° C. to give a white solid which was dissolved in MeOH (8 mL) by gently heating to give a solution. CH3CN (80 mL) was added slowly dropwise via addition funnel at RT to the stirred MeOH solution to give a suspension which was stirred at RT for about 30 min. The solids were filtered, washed with CH3CN thrice, air-dried, then dried in vacuo (0.1 mm Hg) at RT for 16 h to give the titled compound as a white solid (1.390 mg, 70%). The molar ratio of Isometheptene to mucic acid in the salt was 2:1, based on the NMR spectrum: 1H NMR (500 MHz), in D2O: 1H NNMR in CDCl3: 5.16 ppm 1 Ht (J=6.8 Hz), 4.25 ppm 1 Hs, 3.95 ppm 1 Hs, 3.2 ppm 1 Hm, 2.66 ppm 3 Hs, 2.09 ppm 2 Hm, 1.75 ppm 1 Hm, 1.69 ppm 3 Hs, 1.62 ppm 3 Hs, 1.58 ppm 1 Hm, 1.29 ppm 3 Hd (J=7 Hz). MS: mass calc for C9H19N, 141.15. Found: 142.4 (M+H). to give The biphasic solution was stirred at RT for 16 h the aqueous layer was separated extracted with toluene (5×80 mL) (the final extraction with toluene was separated), then the aqueous layer was evaporated in vacuo (1 mm Hg) at 35°-40° C. to give a white solid which by gently heating to give a solution to give a suspension which was stirred at RT for about 30 min The solids were filtered washed with CH3CN thrice air-dried dried in vacuo (0.1 mm Hg) at RT for 16 h