Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 6-Butyl-8-(4-piperidinyloxy)quinoline | HCID 57926048 | — |
| Reactant | HCID 87205857 | HCID 87205857 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 131728653 | HCID 131728653 | 35% |
Reaction Steps
A suspension of 3-(cyclopentylsulfonyl)propyl methanesulfonate (for example, as prepared for Intermediate 25) (0.081 g, 0.3 mmol), 6-butyl-8-(4-piperidinyloxy)quinoline (for example, as prepared for Intermediate 4) (0.102 g, 0.360 mmol), sodium iodide (40 mg, 0.3 mmol) and sodium hydrogen carbonate (200 mg, 2.39 mmol) in dry DMF (2 ml) was heated in a Smith Creator™ microwave oven at 150° C. for 15 min. The reaction mixture was applied to an SCX-2 cartridge (20 g), preconditioned with methanol. The cartridge was washed with methanol (4×25 ml) and then eluted with 10% aqueous 0.88 s.g. ammonia in methanol (4×25 ml). The solvents were removed in vacuo and the resultant residue purified by MDAP to afford the title compound (53 mg): LCMS RT=2.81 min; ES+ve m/z 459 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07884114B2 |
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| Source dataset | uspto-grants-2011_02 |
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| ORD ID | ord-0703e46410774cc2941940a9ec253bf6 |
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| Source note | uspto-grants-2011_02 |
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