Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1H-Indole-5-Carboxylic Acid | HCID 74280 | — |
| Reactant | Diethyl cyanophosphonate | HCID 76257 | — |
| Reactant | 1-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride | HCID 12828501 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 23045036 | HCID 23045036 | 74.8% |
Reaction Steps
To a mixture of indole-5-carboxylic acid (1 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (2.2 g), triethylamine (1.9 g) and N,N-dimethylformamide (20 ml) is added dropwise under ice-cooling diethyl cyanophosphonate (1.5 ml), followed by stirring for 30 minutes under ice-cooling and for further one hour at room temperature. After addition of water (200 ml), ethyl acetate (200 ml) and hexane (50 ml), the reaction mixture is extracted with ethyl acetate. The extract is washed with water, dried, and concentrated. The residue is purified by means of a silica gel column chromatography(hexane:acetone=1:1) to give 1-(5-indolylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine (1.9 g) as a colorless oily product. This product (0.3 g) is led to its fumarate in ethyl ether to obtain colorless powder (0.25 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04937246 |
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| Source dataset | uspto-grants-1990_06 |
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| ORD ID | ord-5782f013af1c429581ea0bf0fd200b37 |
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| Source note | uspto-grants-1990_06 |
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