Triethylamine → (4-Bromo-2,6-dimethyl-phenyl)-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Temperatur

0 °C

A suspension of 0.344 g (1.5 mmol) 4-bromo-2,6-dimethyl-benzoic acid [Fuson, R. C.; Scott, S. L.; Lindsey, R. V., Jr. Journal of the American Chemical Society (1941), 63, 1679-82] in 5 ml of CH2Cl2 was treated at RT with two drops of DMF; then, a solution of 0.14 ml=0.21 g (1.6 mmol) of oxalyl chloride in 3 ml of CH2Cl2 was added drop by drop below 25° C. and the reaction mixture was stirred of 1 hour. After removal of the solvents by evaporation in a high vacuum, the residue was dissolved again in 10 ml of CH2Cl2 and the solution cooled down to 0° C.; then, 0.42 ml=0.30 g (3.0 mmol) of Et3N was added while stirring, followed by 0.23 g (1.5 mmol) of 4-pyrrolidin-1-yl-piperidine. The reaction mixture was subsequently warmed up to RT. After 60 hours, it was poured into crashed ice and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 95:5) to give 0.42 g (76%) of the title compound as light yellow oil. MS: 365.0 (MH+, 1 Br).

1. customAfter removal of the solvents
2. customby evaporation in a high vacuum
3. dissolutionthe residue was dissolved again in 10 ml of CH2Cl2
4. stirringwhile stirring
5. temperatureThe reaction mixture was subsequently warmed up to RT
6. waitAfter 60 hours
7. additionit was poured
8. extractionextracted twice with CH2Cl2
9. washthe organic phases were washed with water
10. dry with materialdried over magnesium sulfate
11. filtrationfiltered
12. customevaporated
13. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 95:5)

ORD-Eintrag

ord-28c52ab0bd084c458d52b1e4c9439e46

Quelldatensatz

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08153805B2