Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ammonium Acetate | HCID 517165 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 58368636 | HCID 58368636 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 58368641 | HCID 58368641 | — |
Reaction Steps
A mixture of 1-[8-(1,4′-bipiperidin-1′-yl)-5-chloroquinolin-7-yl]ethanone (0.0165 g, 0.0444 mmol) and ammonium acetate (0.0342 g, 0.444 mmol) in methanol (0.3 mL) and acetonitrile (0.3 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, to the resulting mixture was added 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.11 mL, 0.11 mmol). The reaction was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with sat. NaHCO3 solution and extracted with dichloromethane. The combined organic phases were dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C21H30ClN4 (M+H)+: m/z=373.2; Found: 373.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680108B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-37e2ea1042504a4d807398b0cc8d283c |
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| Source note | uspto-grants-2014_03 |
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