HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → HCID 68426089, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | HCID 68427487 | HCID 68427487 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 68426089 | HCID 68426089 | 96.9% |
Reaction Steps
A solution of 1-(R)-(4-methoxyphenyl)-N1-[2-(4-methoxyphenyl)ethyl]ethane-1,2-diamine (446 g, 1.48 mol) in ethyl acetate (2.25 L) is placed in a water bath and 1,1′-carbonyldiimidazole (264 g, 1.62 mol) is added in portions. The reaction is then heated to reflux for 1.5 hours after which the solution is cooled, treated with 1N HCl (2×1.5 L), brine (2×1.5 L), dried over Na2SO4 and set aside in the cold. After standing the precipitate which forms is removed by filtration and the solvent removed under reduced pressure to afford 468 g (96% yield) of the desired product. Chiral HPLC of the product thus obtained to have 99.5% of the desired (R) enantiomer present.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07504517B2 |
| Source dataset | uspto-grants-2009_03 |
| ORD ID | ord-89730026afe84821898c198094e13e2c |
| Source note | uspto-grants-2009_03 |