Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Benzyloxybenzyl chloride | HCID 70042 | — |
| Reactant | HCID 10821682 | HCID 10821682 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 23508381 | HCID 23508381 | 61.4% |
Reaction Steps
190 mg of 4-[N-(3-pyridyl)amino]benzonitrile was dissolved in 5 ml of N,N-dimethylformamide, and 44 mg of 60% sodium hydride was added thereto under cooling with ice, followed by stirring at 40-50° C. for 30 minutes. Then, 273 mg of 4-benzyloxybenzyl chloride was added to the reaction mixture under cooling with ice, followed by stirring at room temperature for 2 hours. After the reaction mixture was poured into water, the product was extracted with chloroform. After the extract was washed with water and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting crude product was purified by TLC (using a 1:1 mixture of ethyl acetate and hexane as the developing solvent) to obtain 234 mg of 4-[N-(4-benzyloxy-benzyl)-N-(3-pyridyl)amino]benzonitrile.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06762205B1 |
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| Source dataset | uspto-grants-2004_07 |
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| ORD ID | ord-a847d255ab964665bc7a4c5e7ee2596b |
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| Source note | uspto-grants-2004_07 |
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