Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Acetate | HCID 517165 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | 1-(4-(2-(Diethylamino)ethoxy)phenyl)butan-1-one | HCID 66822369 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 66822143 | HCID 66822143 | 59.4% |
Reaction Steps
Sodium cyanoborohydride (155 mg, 3.5 mmol) was added to a suspension of 1-(4-(2-(diethylamino)ethoxy)phenyl)butan-1-one (21; 186 mg, 0.7 mmol) and ammonium acetate (1.63 g, 21.2 mmol) in methanol (2 mL). The resulting mixture was then heated at 40° C. for 72 hours. The reaction mixture was diluted with ethyl acetate, washed with sat. aqueous NaHCO3 (2×) and sat. brine, dried over sodium sulfate and concentrated to give crude 25 (110 mg, 59%) as a yellow oil: MS (ES+) m/z 265.1 (M+H)+. This material was taken to the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08809377B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-b01838df49f948cb8f3bc197c106841c |
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| Source note | uspto-grants-2014_08 |
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