HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl anisate → 1-{[4-(2,4-Dichlorophenyl)-5-(4-methoxyphenyl)thien-2-yl]carbonyl}-4-phenylpiperidine-4-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl anisate | HCID 8499 | — |
| Reactant | 2,4-Dichlorophenylacetic acid | HCID 88209 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 4-Phenylpiperidine-4-carboxamide | HCID 3017130 | — |
| Reactant | 4-(2,4-Dichlorophenyl)-5-(4-methoxyphenyl)thiophene-2-carboxylic acid | HCID 67299557 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 1-{[4-(2,4-Dichlorophenyl)-5-(4-methoxyphenyl)thien-2-yl]carbonyl}-4-phenylpiperidine-4-carboxamide | HCID 67184695 | 90% |
Reaction Steps
4-(2,4-dichlorophenyl)-5-(4-methoxyphenyethiophene-2-carboxylic acid is prepared, according to the procedure used in stages 1A)-1E), from (2,4-dichlorophenyl)acetic acid and methyl 4-methoxybenzoate. 3.8 g of 4-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)thiophene-2-carboxylic acid, 2.53 g of 4-phenylpiperidine-4-carboxamide (preparation 2), 0.72 ml of Et3N and 3.53 g of TBTU are added at AT to 100 ml of CH2Cl2. The mixture is stirred overnight. It is evaporated to dryness, water is added and the compound obtained is extracted with ethyl acetate. The organic phase is dried and evaporated to dryness. After crystallizing, washing with ethyl ether, filtering and then drying, 5.1 g of the expected compound are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08410137B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-525a0613b454439f994e88bda75255e6 |
| Source note | uspto-grants-2013_04 |