HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-3-hydroxy-5-methoxy-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | 1,4-Dioxane hydrochloride | HCID 20443148 | — |
| Reactant | 3,5-Diethoxy-4-fluoro-benzaldehyde | HCID 59128273 | — |
| Reactant | 3-hydroxy-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride | HCID 68455866 | — |
| Reactant | 4-(3-Hydroxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester | HCID 68458737 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-3-hydroxy-5-methoxy-benzamide | HCID 68455428 | — |
Reaction Steps
In analogy to the procedure described in example 50k), 3-hydroxy-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride [prepared from 4-(3-hydroxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester (example 168a) by Boc cleavage using HCl/dioxane in EtOH at rt in analogy to the procedure described in example 250b)] was reacted with 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless solid. MS: 447.2 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07772253B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-f5fca5315ab14fe2a8ed216f08cf00b6 |
| Source note | uspto-grants-2010_08 |