N-methylheptan-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:; See reaction.notes.procedure_details.

Procedure: Phenyl 4-fluoro-2-nitrophenylcarbamate (0.70 g) and N-methylheptylamine (0.33 g) were dissolved in xylene (5 ml) and the solution was heated under reflux for 2 hrs. The solvent was distilled off and the residue was purified by a silica gel column chromatography (hexane:ethyl acetate=3:1) to give 1-(4-fluoro-2-nitrophenyl)-3-heptyl-3-methylurea as an oily product. the solution was heated under reflux for 2 hrs The solvent was distilled off the residue was purified by a silica gel column chromatography (hexane:ethyl acetate=3:1)

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

Procedure: 0.23 g of sodium are dissolved in 30 ml of 1-heptanol at 50° under nitrogen. Dropwise, with stirring, there is added 4.88 g of N-heptyl-N-methyl-2-bromo-4,5-bibenzyloxycyclopentane-1-amine (obtainable from 3,5-dibenzyloxy-2-cyclopentene by the addition of bromine and reaction with 1-equivalent of methyl heptylamine), dissolved in 30 ml of benzene. Stirring is carried on for 6 hours at 50°. After cooling, 100 ml of benzene is added thereto. This is washed with water. The organic phase is dried over MgSO4 and the solvent is distilled off. After chromatographic purification of the residue (silica gel/chloroform:acetone=9:1), N-heptyl-N-methyl-5-heptyloxy-2,4-dibenzyloxy-cyclopentane-1-amine is obtained. Stirring is carried on for 6 hours at 50° After cooling This is washed with water The organic phase is dried over MgSO4 the solvent is distilled off After chromatographic purification of the residue (silica gel/chloroform:acetone=9:1)

Conditions: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This is an example of Pd/ligand 4-catalyzed aryl amination reaction for aryl amine synthesis. A reaction tube containing NaOtBu (120 mg, 1.25 mmol) was thoroughly evacuated and purged with argon. 5-Chloro-m-xylene (0.14 mL, 1.04 mmol), heptylmethylamine (0.21 mL, 1.25 mmol), a toluene solution of Pd(dba)2 (1.2 mL, 1.0 mg/mL, 2.1 μmol) and a toluene solution of ligand 4 (2.5 mL, 1.0 mg/mL, 6.2 ,μmol) and toluene (0.3 mL) were added to the reaction tube and the reaction was heated at 105° C. for 21.5 h. The reaction was taken up in ether (100 mL) and washed with H2O (30 mL) and brine (30 mL). The organic phase was dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by column chromatography on silica gel using hexanes/ethyl acetate as eluant to afford compound 2 (shown below in Table 1) as a yellowish oil (239 mg, 98%) after drying under vacuum. 1 H NMR (CDCl3): δ6.33 (br, 3H, ArH), 3.25 (t, J=7.6, 2H, —NCH2—), 2.89 (s, 3H, —N—CH3), 2.27 (s, 6H, Ar(CH3)2), 1.54 (br, 2H, —NCH2CH2—), 1.30 (br, 8H, —(CH2)4CH3), 0.89 (br t, J=6.6, 3 H, —CH3). amination reaction was thoroughly evacuated purged with argon washed with H2O (30 mL) and brine (30 mL) The organic phase was dried over MgSO4 filtered concentrated under vacuum The crude product was purified by column chromatography on silica gel

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