Dimethyl Sulfoxide → HCID 53878410, compound

HRID 1657180Notes

Reaction equation

[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.F[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)[CH2:9][CH2:8]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 54.3 grams (0.61 mol) of N-[2'-(2"-hydroxyethoxy)ethyl]piperazine, 50 grams (0.40 mol) of 4-fluorobenzaldehyde, 50 grams of anhydrous potassium carbonate, and 50 mL of DMSO was heated to 120° C. for four days under nitrogen. After cooling to room temperature, the solution was diluted with one liter of water. The aqueous solution was "processed" as follows. It was extracted with dichloromethane; the separated organic layers were combined and dried over anhydrous magnesium sulfate or sodium sulfate. The organic layer was separated, and solvent was removed on a rotary evaporator under reduced pressure (hereafter these steps will be referred to as "processed" and the product was dried under vacuum overnight to afford 75.3 grams (96%) of 4-[4'-(2"-(2'"-hydroxyethoxy)ethyl)piperazino]benzaldehyde (F).

Workup

temperatureAfter cooling to room temperature
extractionIt was extracted with dichloromethane
dry with materialdried over anhydrous magnesium sulfate or sodium sulfate
customThe organic layer was separated
customsolvent was removed on a rotary evaporator under reduced pressure (hereafter these steps
customthe product was dried under vacuum overnight

Sources & evidence

ORD record: ord-2790da6d08f9406bb8ba0df8786b98b4
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05256784

Reaction notes

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