HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → N-Methoxy-N-methyl-4-fluoro-benzenepropanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Isobutyl chloroformate | HCID 62365 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | 3-(4-Fluorophenyl)propionic acid | HCID 136302 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Oxolane--water (1/1) | HCID 21881883 | — |
| Product | N-Methoxy-N-methyl-4-fluoro-benzenepropanamide | HCID 22612404 | 97.8% |
Reaction Steps
A solution of 3-(4-fluorophenyl)propanoic acid (5.0 g, 30 mmol) in THF is cooled in an ice bath and treated with N-methyl morpholine (NMM) (3.0 g, 30 mmol), isobutylchloroformate (4.04 g, 30 mmol) and stirred for few mins. This was then treated with a solution of N,O-Dimethyl hydroxylamine hydrochloride (3.0 g, 30 mmol) in THF/water (neutralized with 3.0 g of NMM) and stirred for 30 minutes. The reaction mixture is diluted with CH2Cl2 and washed successively with 1 N NaOH, water and brine. The solvent was evaporated under vacuum to give 6.2 g of 3-(4-fluorophenyl)-N-methoxy-N-methylpropanamide as oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07291744B2 |
| Source dataset | uspto-grants-2007_11 |
| ORD ID | ord-4c79be0f979d49a38b7d738070a0552e |
| Source note | uspto-grants-2007_11 |