3-methyl-2-phenylbutan-1-amine

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

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

Procedure: The titled compound was prepared from 2-phenyl-3-methylbutylamine (Acta. Pharmaceutica Nordica (1992), 4(2), 105-9) in the same manner as the preparation of N-(2-Phenyl-4-methylpentyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-(3-carboxymethylenephenoxy)propylamine, hydrochloride, Example 189e-h. MS (ESI) 548 (MH+).

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

Procedure: The titled compound was prepared from 2-phenyl-3-methylbutylamine (Acta. Pharmaceutica Nordica (1992), 4(2), 105-9) in the same manner as the preparation of N-(2-Phenyl-4-methylpentyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-(3-carboxymethylenephenoxy)propylamine, hydrochloride, Example 189e-h. MS (ESI) 548 (MH+).

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

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

Procedure: A mixture of 3-methyl-2-phenyl-butylamine (1.3 g, 8 mmol), benzaldehyde (271 μL, 2.66 mmol) and CH2Cl2 (50 mL) is stirred for 20 min at RT. NaBH(OAc)3 (840 mg, 3.96 mmol) and acetic acid (154 μL, 2.69 mmol) are added. After 2 h the same amounts as indicated above of benzaldehyde, NaBH(OAc)3 and acetic acid are added once again. This procedure is repeated after 4 h. After stirring for 16 h at RT, saturated NaHCO3 solution is added, the CH2Cl2 layer is removed and the aqueous phase is extracted twice with fresh CH2Cl2. The combined organic layers are dried (Na2SO4), evaporated in vacuo and the residue is purified by flash chromatography (hexane/ethyl acetate). The combined pure fractions are evaporated to afford the title compound as a colourless oil. MS: 254.3 [M+H]+; tR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 5.03 min. are added once again This procedure is repeated after 4 h After stirring for 16 h at RT the CH2Cl2 layer is removed the aqueous phase is extracted twice with fresh CH2Cl2 The combined organic layers are dried (Na2SO4) evaporated in vacuo the residue is purified by flash chromatography (hexane/ethyl acetate) The combined pure fractions are evaporated

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

Procedure: The title compound is prepared from 3-methyl-2-phenyl-butylamine and benzaldehyde: A solution of 3-methyl-2-phenyl-butylamine (1.3 g, 8 mmol) and benzaldehyde (0.81 mL, 8 mmol) in CH2Cl2 (50 mL) is stirred at RT for 20 min. Sodium triacetoxyborohydride (2.52 g, 11.3 mmol) is then added, followed by acetic acid (0.46 mL, 8 mmol). The reaction mixture is stirred at RT for 16 h, then quenched by the addition of saturated NaHCO3 solution. The organic layer is separated and the aqueous phase is extracted twice with CH2Cl2. The combined organic layers are dried (Na2SO4) and evaporated. The residue is purified by flash chromatography (hexane/ethyl acetate) to afford benzyl-(3-methyl-2-phenyl-butyl)-amine as a colourless oil. MS: 254.3 [M+H]+; tR (HPLC, C18 column; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 5.03 min. quenched by the addition of saturated NaHCO3 solution The organic layer is separated the aqueous phase is extracted twice with CH2Cl2 The combined organic layers are dried (Na2SO4) evaporated The residue is purified by flash chromatography (hexane/ethyl acetate)

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

Procedure: The titled compound was prepared from 2-phenyl-3-methylbutylamine (Acta. Pharmaceutica Nordica (1992), 4(2), 105-9) in the same manner as the preparation of N-(2-Phenyl-4-methylpentyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-(3-carboxymethylenephenoxy)propylamine, hydrochloride, Example 189e-h. MS (ESI) 548 (MH+).