Benzene → Benzyl-{1-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-ethyl}-amine

Temperature

0 °C

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]+.

1. temperaturewas refluxed under N2 for 3 h
2. temperatureAfter cooling
3. filtrationthe mixture was filtered
4. concentrationthe filtrate concentrated in vacuo
5. dissolutionThe crude imine was dissolved in dry THF (3 mL)
6. customquenched with saturated NH4Cl (2 mL)
7. additionAfter diluting with water (10 mL)
8. extractionthe mixture was extracted with CH2Cl2 (2×40 mL)
9. dry with materialThe combined CH2Cl2 extracts were dried over Na2SO4
10. concentrationconcentrated in vacuo
11. customThe residue was purified by column chromatography (silica gel, 40:1 to 20:1 CH2Cl2/MeOH)

ORD record

ord-bf39bb13cd6849369056cdfc91e6f026

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572921B2