Ethanol → 8-Dimethylamino-1-octanol

A solution of 40% dimethylamine/water (30 mL, 26.9 g, 239 mmol) and ethanol (50 mL) was treated with a solution of 8-bromo-1-octanol (15.13 g, 72.3 mmol) and ethanol (20 mL), added dropwise over 10 minutes. The reaction mixture was stirred for 75 hours, diluted with ethyl acetate (80 mL) and washed with saturated sodium bicarbonate solution. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate solution (50 mL) and brine (2×40 mL), dried over sodium sulfate, and concentrated. The 11.4 g of 8-dimethylamino-1-octanol, isolated as a yellow oil, was used as is.

1. additionadded dropwise over 10 minutes
2. washwashed with saturated sodium bicarbonate solution
3. extractionThe aqueous phase was extracted with ethyl acetate
4. washThe combined organic phases were washed with saturated sodium bicarbonate solution (50 mL) and brine (2×40 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated

ORD record

ord-b50f39585fbe47ffb1b77279e97a24f5

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700775B2