Hydrochloric Acid → Sertraline Hydrochloride

HRID 495698Notes

Reaction equation

HRID 495698 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([O-])(=O)C(C1C=CC=CC=1)O.[OH-].[Na+].[ClH:34]>C(OCC)(=O)C.O.C(OCC)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.[ClH:34]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 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 63009Sertraline Hydrochloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2.85 g sertraline free amine (obtained after treating a solution of sertraline mandelate salt in ethyl acetate with a 2 molar solution of NaOH in water, followed by a standard organic work-up procedure) in 300 ml diethyl ether is cooled to 0° C. At this temperature, gaseous HCl is introduced in the reaction mixture for 30 minutes. The reaction mixture, a white suspension, is warmed to room temperature and stirred overnight under an argon atmosphere. The white suspension is filtered and the white product washed with diethyl ether (3×50 ml). The resulting white solid is dried at room temperature by blowing gently a stream of air over the product.

Workup

  1. temperatureThe reaction mixture, a white suspension, is warmed to room temperature
  2. filtrationThe white suspension is filtered
  3. washthe white product washed with diethyl ether (3×50 ml)
  4. customThe resulting white solid is dried at room temperature

Sources & evidence

ORD record
ord-be74995d298d4e4a8df254b2c6922a30
Source dataset
uspto-grants-2005_09
Patent number
US06939992B2

Reaction notes

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