Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 3-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol | HCID 3613517 | — |
| Reactant | HCID 18182198 | HCID 18182198 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 18182340 | HCID 18182340 | 56.5% |
Reaction Steps
5 ml of N,N-dimethylformamide was added to a mixture of 377 mg of 4-benzyl-5-bromo-2-(3,4-methylenedioxyphenyl)thiazole, 178 mg of 3-ethynyl-3-quinuclidinol, 68 mg of tetrakis (triphenylphosphine)palladium(0), 18 mg of cuprous iodide and 0.5 ml of triethylamine, followed by heating under stirring at 100° C. in an oil bath for 15 minutes in a nitrogen atmosphere. After cooling as it was, ethyl acetate and aqueous ammonia were added thereto, and the mixture was extracted with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The resulting crystals were collected by filtration, to give 253 mg of the target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06599917B1 |
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| Source dataset | uspto-grants-2003_07 |
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| ORD ID | ord-299f453fb4d44e8b97341d9032e6611a |
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| Source note | uspto-grants-2003_07 |
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