Hydrochloric Acid → Sertraline Hydrochloride

HRID 347404

Reaction equation

HRID 347404 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]>C(O)CCCCCCC>[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 313Hydrochloric AcidHCID 68617Sertraline

Product 1

HCID 63009Sertraline HydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 9571-OctanolSolvent2×

Procedure

A solution of 53 g free sertraline base in 100 ml of n-octanol was added dropwise over a period of about 30 minutes at room temperature onto 100 ml of n-octanol containing 15 ml of 37% aqueous hydrochloric acid. About half way through the addition a white crystalline solid starts to form. Stirring is maintained for 1 hour then the solid is filtered and washed. It is dried under vacuum. 53.4 g of sertraline hydrochloride form II are obtained with a yield of 90%.

Workup

  1. additionAbout half way through the addition a white crystalline solid starts
  2. customto form
  3. temperatureis maintained for 1 hour
  4. filtrationthe solid is filtered
  5. washwashed
  6. customIt is dried under vacuum

Sources & evidence

ORD record
ord-d13a8d885c5e49518087446e3aa64deb
Source dataset
uspto-grants-2007_02
Patent number
US07173153B2

Linked notes

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