Sodium Hydroxide → HCID 131723760, compound

HRID 1058527Notes

Reaction equation

HRID 1058527 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.[C:21]([O-:31])(=[O:30])[CH:22]([C:24]1C=CC=CC=1)[OH:23].[OH-].[Na+]>O.C(OCC)(=O)C>[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:21]([O-:31])(=[O:30])[C@H:22]([CH3:24])[OH:23]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 131718189(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;2-hydroxy-2-phenylacetate

Product 1

HCID 131723760HCID 131723760, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
15 °C

Procedure

Sertraline mandelate (750 grams) was slurried in a mixture of water (3.9 L) and ethyl acetate (3.9 L). The slurry was cooled to 15° C. NaOH (25% aqueous, 250 mL) was added, resulting in a solution with pH 9.6. The free base of sertraline was partitioned into the ethyl acetate layer which was separated. The aqueous layer was extracted with an additional 3.4 liters of ethyl acetate. The combined ethyl acetate layers were washed with 3.9 liters of water. The ethyl acetate layer containing sertraline base was concentrated under vacuum and filtered to clarify the solution. To this solution was added L-lactic acid (155 g). The reaction mixture was granulated hr 20 hours at room temperature. The solids were filtered, washed 4 times with ethyl acetate(400 mL each time). The crystals were dried overnight under vacuum at 40° C. The yield was calculated to be 84%. mp 153° C.

Workup

  1. customresulting in a solution with pH 9.6
  2. customThe free base of sertraline was partitioned into the ethyl acetate layer which
  3. customwas separated
  4. extractionThe aqueous layer was extracted with an additional 3.4 liters of ethyl acetate
  5. washThe combined ethyl acetate layers were washed with 3.9 liters of water
  6. additionThe ethyl acetate layer containing sertraline base
  7. concentrationwas concentrated under vacuum
  8. filtrationfiltered
  9. additionTo this solution was added L-lactic acid (155 g)
  10. filtrationThe solids were filtered
  11. washwashed 4 times with ethyl acetate(400 mL each time)
  12. customThe crystals were dried overnight under vacuum at 40° C

Sources & evidence

ORD record
ord-2075a3e35a874fe59ba3a2bc08f12fcc
Source dataset
uspto-grants-2003_02
Patent number
US06517866B1

Reaction notes

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