Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 86675137 | HCID 86675137 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86675142 | HCID 86675142 | — |
Reaction Steps
A solution of (E)-2-bromo-N-(piperidin-4-yl)-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzamide (0.1 g, 0.16 mmol), formaldehyde (30% in water) (0.1 mL, 0.16 mmol) and AcOH (0.01 mL) in MeOH (5.0 mL) was stirred at ambient temperature for 30 min After that NaBH3CN (0.01 g, 0.16 mmol) was added at 0° C. and the reaction was stirred for 8 h at ambient temperature. The solvent was removed under reduced pressure to obtain residue which was diluted with EtOAc and washed with saturated aqueous NaHCO3 solution and brine solution. The combined EtOAc layer was dried over Na2SO4 and concentrated under reduced pressure to obtain a residue, which was triturated with Et2O/pentane to afford the title compound as a pale yellow gummy material (0.06 g, 59%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09226500B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-bf54a6ffeed641afafea7089d3c82b63 |
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| Source note | uspto-grants-2016_01 |
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