Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Cyclohexanol | HCID 7966 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 7-Chloro-6-fluoroisoquinoline | HCID 53418922 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 25151202 | HCID 25151202 | — |
Reaction Steps
123.3 mg of 4-aminomethyl-4-phenyl)-cyclohexanol were dissolved in 4 mL of dry DMF and 60 mg of sodium hydride were added. The mixture was allowed to stir for 20 minutes, then 91 mg of 7-Chloro-6-fluoro-isoquinoline (4) were added. Stirring at room temperature was continued until conversion was complete. Ethyl acetate and saturated sodium chloride solution were added. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, concentrated and the resultant residue was purified via preparative HPLC. The obtained TFA salt was dissolved in 2 N HCl and evaporated. After dissolving the residue in water and lyophilization, the title compound was isolated as the hydrochloride. Rt=0.97 min (Method B). Detected mass: 367.2 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08710077B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-a9832df54f85447c8045faf0b808e1a3 |
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| Source note | uspto-grants-2014_04 |
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