Dimethylamine → HCID 22177243, compound

To a solution of 2-(4iodophenyl)-4oxobutyronitrile (2.03 g, 7.1 mmol) in ClCH2CH2Cl (50 mL) was added dimethylamine (14.3 mL, 2M in THF, 28.6 mmol, 4 eq) and the mixture was left stirring at room temperature for 1 h. Na(OAc)3BH (6.04 g, 28.6 mmol, 4 eq) was added and the mixture was stirred at room temperature for 16 h. The reaction was quenched by adding aqueous saturated NaHCO3 (50 mL) and the mixture was extracted with EtOAc (50 mL×3). The organic layer was washed with saturated aqueous NaCl, dried over Na2SO4 and concentrated. The crude product was purified by silica gel chromatography (50% EtOAc/hexanes) to give 4dimethylamino-2-(4iodophenyl)-butyronitrile as a dark brown solid, 2.09 g (94%). 1H NMR (300 MHz, CDCl3): δ 7.83 (d, 2H), 7.22 (d, 2H), 4.10 (t, 1H), 2.56 (m, 1H), 2.41 (m, 1H), 2.34 (s, 6H), 2.20 (m, 1H), 2.05 (m, 1H).

1. waitthe mixture was left
2. stirringthe mixture was stirred at room temperature for 16 h
3. customThe reaction was quenched
4. additionby adding aqueous saturated NaHCO3 (50 mL)
5. extractionthe mixture was extracted with EtOAc (50 mL×3)
6. washThe organic layer was washed with saturated aqueous NaCl
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customThe crude product was purified by silica gel chromatography (50% EtOAc/hexanes)

ORD record

ord-15ebe614985e428d9e91eb5b75a68bb3

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07034056B2