Water → HCID 86613018, compound
Reaction equation
[CH3:1][NH:2][C@@H:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C@H:6]([C:13]2[CH:14]=[CH:15][C:16]([Cl:20])=[C:17]([Cl:19])[CH:18]=2)[CH2:5][CH2:4]1.Cl.[OH-:22].[Na+].[OH2:24]>>[CH3:1][NH:2][C@@H:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C@H:6]([C:13]2[CH:14]=[CH:15][C:16]([Cl:20])=[C:17]([Cl:19])[CH:18]=2)[CH2:5][CH2:4]1.[C:17]([O-:24])(=[O:22])[CH3:18]Participants
Conditions
- Temperature
- 50 °C
Procedure
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.
Workup
- customSertraline base partitioned into the hexane phase
- customThe hexane layer was separated
- extractionThe aqueous layer was extracted a second time with hexane (500 mL)
- additionGlacial acetic acid (23 ml) was added to the solution of sertraline base
- temperatureto cool to room temperature
- stirringstirred at room temperature overnight
- filtrationThe crystals were filtered
- washwashed five times with a total of 250 mL of hexane
- customThe solids were dried at 40° C. in a vacuum oven for 48 hours
Sources & evidence
- ORD record
- ord-ba094dbe5ece45a7b9e2c01d496743c5
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06517866B1
Reaction notes
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