Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 86608145 | HCID 86608145 | — |
| Product | HCID 66638661 | HCID 66638661 | 64% |
Reaction Steps
2-(3-diethylaminomethyl-benzoylamino)-5-formyl-4-methyl-thiophene-3-carboxylic acid ethyl ester (110 mg) synthesized by the above process was dissolved in N,N-dimethylformamide (10 ml), acetic acid (100 μl) and sodium triacetoxyborohydride (66 mg) were added to the solution at room temperature, and the mixture was stirred at that temperature for one hr. After the completion of the reaction, the reaction solution was neutralized with a saturated sodium hydrogencarbonate solution, and was then subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-diethylaminomethyl-benzoylamino)-4-methyl-5-piperidin-1-ylmethylthiophene-3-carboxylic acid ethyl ester (79 mg, yield 64%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08134015B2 |
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| Source dataset | uspto-grants-2012_03 |
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| ORD ID | ord-e67e0901493b45c1acaee5512717bcc3 |
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| Source note | uspto-grants-2012_03 |
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