Methylamine → N-Methyl-1-naphthylamine

Temperatur

-40 °C

Into a solution of 10 g (68 mmol) of α-tetralone in 140 mL of toluene is added 200 mL (400 mmol) of a 2.0 M tetrahydrofuran solution of methylamine at -5° C. to 0° C. After the addition is complete, the reaction mixture is cooled to -40° C. and 34.6 mL (34.6 mmol) of a 1 M solution of titanium tetrachloride in methylene chloride is added over a 15 minute period. After this addition is complete, the reaction mixture is allowed to warm to ambient temperature. After stirring at ambient temperature for 16 hours, the reaction mixture is filtered and the filtrate is concentrated to a crude oil. The crude oil is then dissolved in 150 mL of xylene and 200 mg of 5% palladium on charcoal catalyst is added. The reaction mixture is then heated to reflux for 16 hours. The palladium catalyst is then removed by filtration and the filtrate is concentrated to give 9 g of a crude oil which is purified by flash chromatography (silica gel, 2.5% ethyl acetate in hexane) to give 6 g of an oil in 60% yield.

1. additionAfter the addition
2. additionAfter this addition
3. temperatureto warm to ambient temperature
4. filtrationthe reaction mixture is filtered
5. concentrationthe filtrate is concentrated to a crude oil
6. dissolutionThe crude oil is then dissolved in 150 mL of xylene
7. addition200 mg of 5% palladium on charcoal catalyst is added
8. temperatureThe reaction mixture is then heated
9. temperatureto reflux for 16 hours
10. customThe palladium catalyst is then removed by filtration
11. concentrationthe filtrate is concentrated
12. customto give 9 g of a crude oil which
13. customis purified by flash chromatography (silica gel, 2.5% ethyl acetate in hexane)

ORD-Eintrag

ord-9ae5d0654ec045c19e0950465c2cb4d3

Quelldatensatz

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06054614