N,N,N'-Trimethyl-cyclohexane-1,2-diamine
1. A solution of trans-N,N-dimethyl-1,2-cyclohexanediamine (10 g) and 200 ml of ethyl formate was refluxed 24 h and evaporated.
2. The product, trans-N- [2-(dimethylamino)cyclohexyl]formamide was distilled at bp 104 *C (0.1 mm) 10,2 g (85% yield).
3. A solution of the above N-formyl compound (10.2 g) in 100 ml of ether was added during 5 min to a solution of LAH (10.2 g) in 500 ml of ether and the mixture was refluxed 24 h.
4. It was cooled in ice, decomposed in succession with 10 ml of H2O, 10 ml of 15% NaOH, and 30 ml of H2O, stirred 1h at room temperature, and filtered.
5. The cake was washed with ether, and the solvent was distilled through a Vigreux column.
6. The residue was distilled at bp 86-87 *C (14 mm), 7.65 g (82% yield).
trans-3,4-dichloro-N-[2-(dimethylamino)cyclohexyl]-N-methylbenzamide
1. A solution of 3,4-Dichlorobenzoyl chloride (10 g) in 100 ml of ether was added dropwise during 10 min to a solution of N, N, N'-Trimethyl-cyclohexane-1,2-diamine (7.65 g) in 500 ml of ether containing triethylamine (5 g) while the temperature was maintained at 20-26 *C.
2. The resulting suspension was stirred at room temperature 24 h.
3. Saturated NaHCO3 solution (250 ml) was added, the ether layer was separated, and the aqueous was extracted once with ether.
4. The combined ether extract was washed with H2O and saturated salt solution, dried (MgSO4), and evaporated to gave 11 g.
7. The free base was converted to the salt (HCl or another).
1. A solution of trans-N,N-dimethyl-1,2-cyclohexanediamine (10 g) and 200 ml of ethyl formate was refluxed 24 h and evaporated.
2. The product, trans-N- [2-(dimethylamino)cyclohexyl]formamide was distilled at bp 104 *C (0.1 mm) 10,2 g (85% yield).
3. A solution of the above N-formyl compound (10.2 g) in 100 ml of ether was added during 5 min to a solution of LAH (10.2 g) in 500 ml of ether and the mixture was refluxed 24 h.
4. It was cooled in ice, decomposed in succession with 10 ml of H2O, 10 ml of 15% NaOH, and 30 ml of H2O, stirred 1h at room temperature, and filtered.
5. The cake was washed with ether, and the solvent was distilled through a Vigreux column.
6. The residue was distilled at bp 86-87 *C (14 mm), 7.65 g (82% yield).
trans-3,4-dichloro-N-[2-(dimethylamino)cyclohexyl]-N-methylbenzamide
1. A solution of 3,4-Dichlorobenzoyl chloride (10 g) in 100 ml of ether was added dropwise during 10 min to a solution of N, N, N'-Trimethyl-cyclohexane-1,2-diamine (7.65 g) in 500 ml of ether containing triethylamine (5 g) while the temperature was maintained at 20-26 *C.
2. The resulting suspension was stirred at room temperature 24 h.
3. Saturated NaHCO3 solution (250 ml) was added, the ether layer was separated, and the aqueous was extracted once with ether.
4. The combined ether extract was washed with H2O and saturated salt solution, dried (MgSO4), and evaporated to gave 11 g.
7. The free base was converted to the salt (HCl or another).
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