Dimethyl Sulfoxide → 3-(4-(4-Methylpiperazin-1-yl)phenyl)butanenitrile

HRID 1896281Notes

Reaction equation

[C:1]([CH:3]([CH:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)[CH3:9])C(OC)=O)#[N:2].[Cl-].[Na+].CS(C)=O>O>[CH3:22][N:19]1[CH2:20][CH2:21][N:16]([C:13]2[CH:14]=[CH:15][C:10]([CH:8]([CH3:9])[CH2:3][C:1]#[N:2])=[CH:11][CH:12]=2)[CH2:17][CH2:18]1

Participants

Conditions

Temperature: 162.5 °C

Procedure

A mixture of methyl 2-cyano-3-(4-(4-methylpiperazin-1-yl)phenyl)butanoate (700 mg, 2.32 mmol), sodium chloride (405 mg, 6.90 mmol), DMSO (5 ml) and water (2 ml, 3 vol %) and heated at 160-165° C. for 12 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford 450 mg (79.6%) of 3-(4-(4-methylpiperazin-1-yl)phenyl)butanenitrile as a colorless liquid.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-94792f34f16a4be9b42e843a48acf1f4
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518948B2

Reaction notes

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