N-methylhexan-1-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: At 0° to 5° C., 11.5 g (0.10 mol) of N-methylhexylamine in 100 ml of tetrahydrofuran was added to a solution of 12.3 g (0.05 mol) of 2-chloro5-nitrocinnamyl chloride in 40 ml of tetrahydrofuran. After the mixture had been stirred for 2 hours, the solvent was removed, and the residue thus obtained was dissolved in ethyl acetate and extracted with 5% strength sodium hydroxide solution. The organic phase was washed with water, followed by separation and drying, to give 13.3 g (81% of theory) of 2-chloro-5-nitrocinnamic acid-N-methyl-N-hexylamide. the solvent was removed the residue thus obtained extracted with 5% strength sodium hydroxide solution The organic phase was washed with water followed by separation drying

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

Procedure: At 0° to 5° C., 11.5 g (0.10 mol) of N-methylhexylamine in 100 ml of tetrahydrofuran was added to a solution of 12.3 g (0.05 mol) of 2-chloro5-nitrocinnamyl chloride in 40 ml of tetrahydrofuran. After the mixture had been stirred for 2 hours, the solvent was removed, and the residue thus obtained was dissolved in ethyl acetate and extracted with 5% strength sodium hydroxide solution. The organic phase was washed with water, followed by separation and drying, to give 13.3 g (81% of theory) of 2-chloro-5-nitrocinnamic acid-N-methyl-N-hexylamide. the solvent was removed the residue thus obtained extracted with 5% strength sodium hydroxide solution The organic phase was washed with water followed by separation drying

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 0.35 ml of (i-Pr)2NEt in 10 ml of diethyl ether at 0° C. was added phosgene (1.06 ml, 1.93 M solution in toluene) and N-hexylmethylamine (0.31 ml, 2.05 mm). The reaction mixture was allowed to warm up to 25° C., and further stirred at 25° C. for 14 h. The mixture was filtered, and the solvent was removed under vacuum. The product was used for the next step reaction without further purification. 1H NMR (CDCl3): δ 3.42 (m, 2H),.3.07 (s, 3H), 1.59 (m, 2H), 1.31 (m, 6H), 0.90 (m, 3H). The mixture was filtered the solvent was removed under vacuum The product was used for the next step reaction without further purification

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

Procedure: Starting with 5-[4-(9H-9-carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoic acid (0.12 g, 0.21 mmol) prepared in Example 128 and N-hexyl-N-methylamine (0.3 ml), the same procedure as shown in Example 129 was repeated to give the titled compound (0.10 g, yield: 71%) as a white powder (cis:trans=3:1).

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

Procedure: Starting with 5-[4-(9H-9-carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoic acid (0.12 g, 0.21 mmol) prepared in Example 128 and N-hexyl-N-methylamine (0.3 ml), the same procedure as shown in Example 129 was repeated to give the titled compound (0.10 g, yield: 71%) as a white powder (cis:trans=3:1).

Conditions: temp:0.00; pressure:0.00; stir: