HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanamine, N-methoxy-, hydrochloride (1:1) → 3-tert-Butyl-N-methoxy-N-methyl-5-[3-(tetrahydropyran-2-yloxy)propoxy]benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733286 | — |
| Reactant | 3-tert-Butyl-5-[3-(tetrahydropyran-2-yloxy)propoxy]benzoic acid | HCID 58136832 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-tert-Butyl-N-methoxy-N-methyl-5-[3-(tetrahydropyran-2-yloxy)propoxy]benzamide | HCID 58136958 | 99.4% |
Reaction Steps
3-tert-Butyl-5-[3-(tetrahydropyran-2-yloxy)propoxy]benzoic acid (O4.059; 4.90 g) and N,O-dimethylhydroxylaminehydrochloride (1.42 g) were dissolved in DMF (80 ml) and admixed with Hünig's base (4.81 ml) and TOTU (4.78 g). After stirring for 2 h, the mixture was left to stand overnight. Then the DMF was drawn off, the mixture was partitioned between EA and saturated sodium hydrogencarbonate solution, and the EA phase was removed, dried over magnesium sulfate, filtered and concentrated. 5.49 g of the title compound were obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08198272B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-aa8b3e8f1c4a4b8c90256da1b6eea2b5 |
| Source note | uspto-grants-2012_06 |