Sertraline → Sertraline Hydrochloride

HRID 853175Notes

Reaction equation

HRID 853175 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].CC(N(C)C)=O>C(#N)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:21]

Participants

4

Reactant 2

HCID 68617SertralineHCID 523006HCID 523006, compound

Product 1

HCID 63009Sertraline HydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

3 g sertraline base is dissolved in 45 ml acetonitrile at room temperature. The solution is cooled to 0° C. whereby a suspension is formed. A solution of 1.33 g dimethylacetamide hydrochloride in 15 ml acetonitrile is added under stirring within one minute. During the addition of the solution the temperature increases to about 8° C. and sertraline hydrochloride precipitates. After stirring for one hour at 0° C. the crystalline product is filtered off and dried at 50° C. under vacuum to yield 3.28 g (98%) of sertraline hydrochloride form II.

Workup

  1. customis formed
  2. additionDuring the addition of the solution the temperature
  3. temperatureincreases to about 8° C.
  4. customsertraline hydrochloride precipitates
  5. stirringAfter stirring for one hour at 0° C. the crystalline product
  6. filtrationis filtered off
  7. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-82705be393044ea2aff45c4d6db069f7
Source dataset
uspto-grants-2007_08
Patent number
US07253320B2

Reaction notes

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