Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Diethylamine | HCID 8021 | — |
| Reactant | HCID 19600103 | HCID 19600103 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | HCID 19600144 | HCID 19600144 | — |
Reaction Steps
To a solution of 0.269 g (0.807 mmol) of 5-(5-phenylpentylsulfonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 20 ml of acetic acid, 0.10 ml (0.97 mmol) of diethylamine and 79 mg (0.97 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 30 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=9/1) to yield the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05998433 |
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| Source dataset | uspto-grants-1999_12 |
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| ORD ID | ord-b1d4981efb5d457c97ab023daf3987d2 |
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| Source note | uspto-grants-1999_12 |
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