Hydrochloric Acid → 1-(3,4-Dimethoxyphenyl)-N-methyl-2-propanamine

Temperature

4 °C

A solution of 15.1 g (78 mmol) of (3,4-dimethoxyphenyl)acetone (1) in 102 mL of methanol was cooled to 4° C. and was treated with 35 mL of 40% aqueous methylamine. To the reaction mixture, 3.5 g (92.5 mmol) of sodium borohydride was then added, and the temperature of the reaction was maintained at 4° C. The reaction mixture was allowed to stir for an additional 30 minutes, then concentrated under reduced pressure. To the residue, 60 mL of water was added, and the resulting reaction mixture was acidified to pH 1 using 6N HCl. The aqueous layer was extracted with 5×50 mL of dichloromethane, and the pH was adjusted to pH 13 using 6N NaOH. The aqueous layer was extracted with 4×75 mL of dichloromethane. The organic layers were combined, dried and concentrated to give 15 g (72 mmol, 92%) of 1A as a colorless oil (M+H, 210).

1. concentrationconcentrated under reduced pressure
2. additionTo the residue, 60 mL of water was added
3. customthe resulting reaction mixture
4. extractionThe aqueous layer was extracted with 5×50 mL of dichloromethane
5. extractionThe aqueous layer was extracted with 4×75 mL of dichloromethane
6. customdried
7. concentrationconcentrated

ORD record

ord-26b63cefb36f4547a85b06b7b0e4a423

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569676B2