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

HRID 131407Notes

Reaction equation

CS(C)=O.[C:5](Cl)(=[O:9])[C:6](Cl)=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][CH:19]1C(O)C)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl.C(OCC)(=O)C>[CH2:11]([N:18]1[CH2:19][CH2:20][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:22][C@@H:23]1[CH2:6][CH:5]=[O:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Add anhydrous DMSO (3.57 mL, 50.25 mmol) in anhydrous dichloromethane (68.0 mL). Cool to −78° C. and stir. Add oxalyl chloride (2M in dichloromethane, 12.06 mL, 24.125 mmol) dropwise. Stir at −78° C. for 30 minutes. Add (1,4-dibenzyl-piperazin-2-yl)-ethanol (6.241 g, 20.1 mmol) in dichloromethane (12.0 mL) and stir. After 1 hour, add triethylamine (14.01 mL, 100.5 mmol) and stir for another 1 hour. Allow the reaction mixture gradually warm to ambient temperature. Add saturated ammonium chloride. (200 mL). Exact aqueous portion with ethyl acetate three times. Combine the organic solution, dry over sodium sulfate, filter, and concentrate under reduced pressure to give crude residue. Purify the residue by flash chromatography, eluting with 2M ammonia in methanol:dichloromethane (5:95) to give the title compound: mass spectrum (m/e):309.03 (M+1).

Workup

stirringStir at −78° C. for 30 minutes
stirringstir for another 1 hour
temperaturegradually warm to ambient temperature
dry with materialCombine the organic solution, dry over sodium sulfate
filtrationfilter
concentrationconcentrate under reduced pressure
customto give crude residue
customPurify the residue by flash chromatography
washeluting with 2M ammonia in methanol:dichloromethane (5:95)

Sources & evidence

ORD record: ord-4a4d8c8437d7447c8ad4a28c3d1278f3
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

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