Sertraline → Sertraline Hydrochloride

HRID 458229Notes

Reaction equation

HRID 458229 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.[ClH:21].N1C=CC=CC=1>C(O)CC>[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:21]

Participants

4

Reactant 2

HCID 68617SertralineHCID 10176127Pyridinium chloride

Product 1

HCID 63009Sertraline Hydrochloride

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A solution of 50 g of sertraline base in 200 ml of n-propanol is treated with one equivalent of pyridine hydrochloride at 50° C., under a nitrogen atmosphere, for about half an hour. The mixture is allowed to reach room temperature. At about 45° C. a gel begins to precipitate which fluidifies rapidly and transforms into a crystalline solid. Agitation is maintained for 1 hour at room temperature. The solid is filtered, washed and dried under vacuum. 52 g of sertraline hydrochloride form II (yield 93%) are obtained.

Workup

  1. customto reach room temperature
  2. customAt about 45° C.
  3. customto precipitate which
  4. filtrationThe solid is filtered
  5. washwashed
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ccb6519f09f24a21912630178840ad80
Source dataset
uspto-grants-2007_03
Patent number
US07189876B2

Reaction notes

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