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 acetic acid (0.01 mL) in methanol (5.0 mL) was stirred at RT 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 RT. The solvent was removed under reduced pressure to obtain residue which was diluted with ethyl acetate and washed with saturated aq. NaHCO3 solution and brine solution. The combined ethyl acetate layer was dried over Na2SO4 and concentrated under reduced pressure to obtain a residue, which was triturated with diethyl ether/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 | US09212164B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-a206e31f973d4edc84d355442441fce8 |
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| Source note | uspto-grants-2015_12 |
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