Benzene → Benzyl-{1-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-ethyl}-amine
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH:11]=O.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH:25]1C=CC=CC=1>>[CH2:17]([NH:24][CH:11]([C:7]1[N:6]([CH2:5][C:4]2[CH:3]=[C:2]([Cl:1])[CH:15]=[C:14]([Cl:16])[CH:13]=2)[CH:10]=[CH:9][N:8]=1)[CH3:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 1-(3,5-dichloro-benzyl)-1H-imidazole-2-carbaldehyde (see Example 2) (128 mg, 0.50 mmol), benzylamine (64 mg, 0.60 mmol), 3A molecular sieves (100 mg) and benzene (5 mL) was refluxed under N2 for 3 h. After cooling, the mixture was filtered and the filtrate concentrated in vacuo. The crude imine was dissolved in dry THF (3 mL) and the solution cooled to 0° C. before addition of MeMgBr (0.2 mL of a 3N solution in THF, 0.6 mmol). The resulting mixture was stirred at 0° C. for 1 h and then quenched with saturated NH4Cl (2 mL). After diluting with water (10 mL), the mixture was extracted with CH2Cl2 (2×40 mL). The combined CH2Cl2 extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 40:1 to 20:1 CH2Cl2/MeOH) to provide the title compound (60 mg, 33%) as a colorless oil: ESI MS m/z 360 [C19H19Cl2N2+H]+.