Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 19028848 | HCID 19028848 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 19029014 | HCID 19029014 | 154% |
Reaction Steps
To a solution of 4-(p-chlorophenyl)-4-[3-(4-phenylpiperazin-1-yl)propyl]-1,2,3,4-tetrahydroisoquinoline (0.7 g) in acetonitrile (15 ml) was added formalin (0.64 ml). Then, sodium cyanoborohydride (0.16 g) was added portionwise with stirring. The mixture was stirred for 15 minutes, at the end of which time acetic acid was added dropwise until the solution became neutral. The mixture was further stirred for 2 hours and the reaction mixture was extracted with ethyl acetate-1N aqueous sodium hydroxide solution. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified by silica gel column chromatography and treated with hydrochloric acid to provide the title compound (0.6 g) as colorless powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05607939 |
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| Source dataset | uspto-grants-1997_03 |
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| ORD ID | ord-97b7a2679dc14c59b163ccf3cd73a5f2 |
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| Source note | uspto-grants-1997_03 |
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