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

HRID 131396Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][C@@H:19]1[CH2:31][CH2:32][OH:33])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.C(=O)(O)[O-].[Na+]>[CH2:11]([N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][C@@H:19]1[CH2:31][CH:32]=[O:33])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

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).

Workup

temperaturewarm to room temperature overnight
extractionextract three times with dichloromethane
dry with materialdry over sodium sulfate
concentrationconcentrate under reduced pressure
customPurify by flash chromatography
washeluting with a step gradient

Sources & evidence

ORD record: ord-ce0d6865288148c9a95bf43626dba680
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

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