Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzaldehyde | HCID 240 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 178419017 | HCID 178419017 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 14712103 | HCID 14712103 | — |
Reaction Steps
Compound XIIIA is prepared by treatment of a mixture of compound XIIA, histamine, and benzaldehyde in a solvent such as MeOH or EtOH, with a reducing agent such as NaBH4 to provide N-benzyl-2-(1H-imidazol-5-yl)ethanamine (compound not shown). To this compound in water at 0° C., is added KOH followed by acetaldehyde. After approximately six hours at 80° C. followed by treatment with acid, compound XIIIA, PG=Bn, is isolated. Trifluoromethyl derivative XIVA is also prepared from compound XIIA. To a solution of compound XIIA in a solvent such as water at a temperature of about 0° C., is added a base such as KOH along with trifluoroacetaldehyde. After heating at a temperature of approximately 80° C. for approximately 6 hours and acidification, compound XIVA is isolated.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09066946B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-7c6ab23cafe844dbb784c255d3711865 |
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| Source note | uspto-grants-2015_06 |
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