Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-(Trimethylsilyl)benzaldehyde | HCID 637573 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 2-[3-(Trifluoromethoxy)phenyl]ethan-1-amine hydrochloride | HCID 57438503 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 25179430 | HCID 25179430 | 100.7% |
Reaction Steps
4-Trimethylsilanyl-benzaldehyde (178 mg, 1 mmol), 2-(3-trifluoromethoxy-phenyl)-ethyl-amine hydrochloride (241 mg, 1.1 mmol) and triethyl amine (151 mg, 1.5 mmol) were dissolved in methanol (5 ml) and the solution was stirred at rt for 5 min. Sodium borohydride (37 mg, 1 mmol) was added under nitrogen and the reaction mixture was stirred at rt for 1 h. Water was added and methanol was evaporated in vacuo. The reaction was extracted twice with diethyl ether and the combined organic layers were washed once with water and once with sat. aq. NaCl solution, dried with sodium sulfate, filtered off and concentrated in vacuo to yield [2-(3-trifluoromethoxy-phenyl)-ethyl]-(4-trimethylsilanyl-benzyl)-amine (370 mg, 100%) as a colorless oil. MS (ISP) 368.2 (100) (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07572823B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-9fce47b64154467ebe06bb2fd9e7f25d |
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| Source note | uspto-grants-2009_08 |
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