Dimethyl Sulfoxide → 1-Isopropyl-piperidine-4-carboxaldehyde

Temperature

-70 °C

Oxalyl chloride (3.15 ml) was dissolved in 30 ml of dichloromethane, a solution of 3.20 ml of dimethyl sulfoxide in 6 ml of dichloromethane was added thereto at −70° C., the mixture was stirred for 15 minutes, a solution of 2.93 g of (1-isopropyl-4-piperidyl)methanol in 15 ml of dichloromethane was added thereto at −70° C. and the mixture was stirred for 1 hour. After 12.5 ml of triethylamine were added at −70° C., the mixture was raised to room temperature, then water and a saturated aqueous solution of sodium hydrogen carbonate were added and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated in vacuo and ethyl acetate was added to the resulting residue. After removing the insoluble matter by filtration, the solvent was evaporated in vacuo to give 1.15 g of 1-isopropylpiperidine-4-carbaldehyde. This compound was used for the next reaction without purification.

1. stirringat −70° C. and the mixture was stirred for 1 hour
2. temperaturethe mixture was raised to room temperature
3. extractionthe mixture was extracted with chloroform
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. customthe solvent was evaporated in vacuo and ethyl acetate
6. additionwas added to the resulting residue
7. customAfter removing the insoluble matter
8. filtrationby filtration
9. customthe solvent was evaporated in vacuo

ORD record

ord-f557ff94a62c40dcb20eb8ef6d562520

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504417B2