HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → N-[1-(4-Chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-3-hydroxymethyl-5-methoxy-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | Diisobutylaluminumhydride | HCID 21225700 | — |
| Reactant | 4-Chloro-3,5-diethoxybenzaldehyde | HCID 59210375 | — |
| Reactant | 4-Chloro-3,5-diethoxybenzoic acid ethyl ester | HCID 59684773 | — |
| Reactant | N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-3-hydroxymethyl-5-methoxy-benzamide | HCID 68458782 | — |
| Catalyst | Manganese dioxide | HCID 14801 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | N-[1-(4-Chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-3-hydroxymethyl-5-methoxy-benzamide | HCID 68456379 | — |
Reaction Steps
In analogy to the procedure described in example 50k), 3-hydroxymethyl-5-methoxy-N-piperidin-4-yl-benzamide (example 217) was reacted with 4-chloro-3,5-diethoxy-benzaldehyde [prepared from 4-chloro-3,5-diethoxy-benzoic acid ethyl ester (example 219a) by reduction with di-isobutylaluminium hydride followed by oxidation with MnO2 in analogy to the procedures described in example 1a)], sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless oil. MS: 477.0 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07772253B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-e98e0ed8fbc04ac0b8b417e58f2f167a |
| Source note | uspto-grants-2010_08 |