Cesium carbonate → 4-{[(4-Dipropylamino-butyl)-phenyl-amino]-methyl}-benzonitrile

HRID 2080788Notes

Reaction equation

[C:1]1([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=1>CN(C=O)C>[CH2:13]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:11][CH2:10][CH2:9][CH2:8][N:7]([CH2:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:14][CH3:15]

Participants

Conditions

Temperature: 60 °C

Procedure

The compound (152.5 mg) obtained in Example 24-1 was dissolved in anhydrous DMF (6.1 ml) and added with cesium carbonate (299.0 mg) and 4-bromomethyl-benzonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (184.0 mg). The whole was stirred overnight at 60° C. and then stirred at 80° C. for additional 24 hours. After completion of the reaction, the solvent was distilled off. The resultant was added with water, subjected to extraction with chloroform, and dried with magnesium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (88.8 mg) as a colorless oily substance.

Workup

stirringstirred at 80° C. for additional 24 hours
customAfter completion of the reaction
distillationthe solvent was distilled off
additionThe resultant was added with water
extractionsubjected to extraction with chloroform
dry with materialdried with magnesium sulfate
distillationThe solvent was distilled off
customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-3a822c35debb441c837e860e6bdee4b1
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932281B2

Reaction notes

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