HuagongsheHuagongshe Chemistry Print Report · For research reference only
Morpholine → N-(3-Iodo-4-methyl-phenyl)-6-morpholin-4-yl-nicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-chloro-N-(3-iodo-4-methyl-phenyl)-nicotinamide | HCID 7925562 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-(3-Iodo-4-methyl-phenyl)-6-morpholin-4-yl-nicotinamide | HCID 17541675 | — |
Reaction Steps
A mixture of 6-chloro-N-(3-iodo-4-methyl-phenyl)-nicotinamide (50 mg, 0.13 mmol) and morpholine (35 mg, 0.42 mmol), diisopropylethyl amine (0.07 mL, 0.42 mmol) and a catalytic amount of DMAP in dioxane (5 mL) was heated at 120° C. in a sealed tube until consumption of the limiting reagent. The mixture was then cooled and partitioned between EtOAc and water. Organic layer was removed, dried over Na2SO4 filtered and concentrated to a residue that after a silica gel column with 20-40% EtOAc in hexanes gradient afforded the product. HRMS m/z calcd for C17H18N3O2I [M+H]+: 424.0517. Found: 424.0516.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08324385B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-f286f29b0c4d4e45999e1ba142c09410 |
| Source note | uspto-grants-2012_12 |