HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → N-diaminomethylene-3-methylsulphonyl-4-(4-BOC-aminopiperidino)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Carbamimidoylazanium Chloride | HCID 5460839 | — |
| Reactant | Methyl 4-Fluoro-3-(methylsulfonyl)benzoate | HCID 10752025 | — |
| Reactant | 6-chloro-N-methylpyridinium chloride | HCID 11744962 | — |
| Reactant | Tert-butyl 1-aminopiperidine-4-carboxylate | HCID 21899493 | — |
| Reactant | 3-methylsulphonyl-4-(4-BOC-aminopiperidino)benzoic acid | HCID 67789078 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | N-diaminomethylene-3-methylsulphonyl-4-(4-BOC-aminopiperidino)benzamide | HCID 70199108 | — |
Reaction Steps
1.0 g of 3-methylsulphonyl-4-(4-BOC-aminopiperidino)benzoic acid [obtainable by reacting methyl 3-methylsulphonyl-4-fluorobenzoate with 4-BOC-aminopiperidine and subsequently hydrolyzing the product to give the free acid] is dissolved in 15 ml of 1-methylpyrrolidone, and 0.67 g of 1-methyl-2-chloropyridinium chloride is added to this solution, which is stirred for 15 min. 0.9 g of guanidinium chloride and 2.6 ml of diisopropylethylamine are then added and the mixture is stirred at room temperature for 1 hr. After customary working-up, and after chromatography on silica gel (flash process, ethylacetate/10% methanol), N-diaminomethylene-3-methylsulphonyl-4-(4-BOC-aminopiperidino)benzamide is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05461066 |
| Source dataset | uspto-grants-1995_10 |
| ORD ID | ord-e67c2546347d447192afd83a9ba9cf62 |
| Source note | uspto-grants-1995_10 |