Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| Reactant | HCID 70556657 | HCID 70556657 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86725373 | HCID 86725373 | — |
Reaction Steps
A mixture of the product of Example 14B (45 mg, 0.17 mmol), tert-butyl piperazine-1-carboxylate (38 mg, 0.2 mmol), tetrabutylammonium bromide (6 mg, 0.02 mmol) and potassium carbonate (35 mg, 0.26 mmol) in dry DMSO (5 mL) was heated under nitrogen at 120° C. for 3 hours. The mixture was added to water (20 mL) and aqueous hydrogen chloride solution (20 mL) and washed with ethyl acetate. The aqueous phase was basified with 2.5N sodium hydroxide solution and extracted with ethyl acetate (3×20 mL). The combined organic phase was dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 40/1 dichloromethane/methanol to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09212192B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-04860c4f9140491cba2304aff332a4b4 |
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| Source note | uspto-grants-2015_12 |
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