Dimethyl Sulfoxide → (S)-(1,4-dibenzyl-piperazin-2-yl)-acetaldehyde

Temperature

-78 °C

Combine a solution of oxalyl chloride (0.1.83 mL, 21.0 mmol) in dichloromethane (20 mL) with a solution of dimethyl sulfoxide (2.34 mL, 33.0 mmol) in dichloromethane (10 mL) at −78° C. and stir for 15 minutes. Add a solution of (S)-2-(1,4-dibenzylpiperazin-2-yl)ethanol (0.60 g, 1.82 mmol) in dichloromethane (10 mL) at −78° C. via cannula. Stir at −78° C. for one hour, add triethylamine (10.5 mL, 75.0 mmol) and warm to room temperature overnight. Dilute the mixture with saturated aqueous sodium bicarbonate and extract three times with dichloromethane. Combine the organic layers, dry over sodium sulfate and concentrate under reduced pressure. Purify by flash chromatography, eluting with a step gradient starting with dichloromethane going to 6% 2N ammonia-methanol in dichloromethane to obtain the title compound (3.66 g, 11.9 mmol, 79%) as a brown oil: mass spectrum (APCI): m/z=309.4 (M+1).

1. temperaturewarm to room temperature overnight
2. extractionextract three times with dichloromethane
3. dry with materialdry over sodium sulfate
4. concentrationconcentrate under reduced pressure
5. customPurify by flash chromatography
6. washeluting with a step gradient

ORD record

ord-ce0d6865288148c9a95bf43626dba680

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07384934B2