Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Sertraline Hydrochloride | HCID 63009 | — |
| Product | HCID 86613018 | HCID 86613018 | 89% |
Reaction Steps
Sertraline hydrochloride (125 g) was slurried in a mixture of water (1 L) and (2.5 L). NaOH (25% aqueous, 35 mL) was added. Sertraline base partitioned into the hexane phase. The hexane layer was separated. The aqueous layer was extracted a second time with hexane (500 mL). The hexane layers were combined. The solution of sertraline base in hexane was heated to 50° C. Glacial acetic acid (23 ml) was added to the solution of sertraline base. The reaction mixture was stirred at 50° C. for 30minutes. The reaction mixture was allowed to cool to room temperature and stirred at room temperature overnight. The crystals were filtered and washed five times with a total of 250 mL of hexane. The solids were dried at 40° C. in a vacuum oven for 48 hours. The yield was 89%. mp 126° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06517866B1 |
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| Source dataset | uspto-grants-2003_02 |
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| ORD ID | ord-ba094dbe5ece45a7b9e2c01d496743c5 |
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| Source note | uspto-grants-2003_02 |
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