4-Aminophenol → 4-[2-(Dimethylamino)ethoxy]aniline

1-Chloro-2-dimethylaminoethane hydrochloride (2 g, 21.9 mmol, 1.2 equiv) was added in one portion to a mixture of 4-aminophenol (2 g, 18.3 mmol) and finely powdered sodium hydroxide (1.8 g, 45.8 mmol, 2.5 equiv) in DMF (27 mL), under an argon atmosphere. The reaction mixture was stirred for 17 h at rt. The resulting dark suspension was filtered. The filtrate was diluted with DCM (200 ml) and washed with brine (2×50 mL). The organic phase was dried (Na2SO4), filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/MeOH, 7:3) provided 3 g of the title compound as a brown solid: API-MS: 181.2 [M+H]+; TLC: Rf=0.18 (DCM/MeOH, 7:3).

1. filtrationThe resulting dark suspension was filtered
2. additionThe filtrate was diluted with DCM (200 ml)
3. washwashed with brine (2×50 mL)
4. dry with materialThe organic phase was dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customPurification of the residue by silica gel column chromatography (DCM/MeOH, 7:3)

ORD record

ord-d86d906d657748089f0a6b139f94b43b

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674099B2