HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → [4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidinyl-1'-yl]-(3-methanesulfonyl-phenyl)-methanone acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-Methanesulfonylbenzoic acid | HCID 220380 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | PyBroP | HCID 2733179 | — |
| Reactant | 4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidine | HCID 22397434 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | [4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidinyl-1'-yl]-(3-methanesulfonyl-phenyl)-methanone acetate | HCID 22397435 | 73.1% |
Reaction Steps
The product of Step b (0.15 g) was dissolved in THF (4 ml), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PYBROP™; 0.235 g), 3-methylsulphonylbenzoic acid (0.091 g) and N,N-di-iso-propylethylamine (0.238 ml) were added. After 18 hours at room temperature ethyl acetate and aqueous NaHCO3 solution were added. The product was extracted with ethyl acetate, the combined organic extracts dried with Na2SO4 and concentrated. Purification by reverse phase HPLC (with a gradient eluent system (45% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%)) gave the title compound (0.095 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06525070B2 |
| Source dataset | uspto-grants-2003_02 |
| ORD ID | ord-5444b2f23f074b858538786132a5c9ff |
| Source note | uspto-grants-2003_02 |