Hydrochloric Acid → Sertraline Hydrochloride

HRID 347405Notes

Reaction equation

HRID 347405 reaction equation
[ClH:1].[CH3:2][NH:3][C@@H:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C@H:7]([C:14]2[CH:15]=[CH:16][C:17]([Cl:21])=[C:18]([Cl:20])[CH:19]=2)[CH2:6][CH2:5]1>C(O)CC>[CH3:2][NH:3][C@@H:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C@H:7]([C:14]2[CH:15]=[CH:16][C:17]([Cl:21])=[C:18]([Cl:20])[CH:19]=2)[CH2:6][CH2:5]1.[ClH:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68617Sertraline

Product 1

HCID 63009Sertraline HydrochlorideYield 88%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of 15 ml of aqueous hydrochloric acid 37% in 100 ml of n-propanol was heated at 45° C. and a solution of 50 g free sertraline base in 100 ml of n-propanol was added dropwise over a period of about 30 minutes. About 20 minutes after the end of the addition a white crystalline solid starts to form. The suspension is stirred for 1 hour at 45° C., then cooled to room temperature within 1 hour. The solid is filtered, washed and dried under vacuum. 49.2 g of sertraline hydrochloride form II are obtained in a 88% yield.

Workup

  1. additionAbout 20 minutes after the end of the addition a white crystalline solid starts
  2. customto form
  3. temperaturecooled to room temperature within 1 hour
  4. filtrationThe solid is filtered
  5. washwashed
  6. customdried under vacuum

Sources & evidence

ORD record
ord-75f5f2a9b4c2459ca7fb639a9a579558
Source dataset
uspto-grants-2007_02
Patent number
US07173153B2

Reaction notes

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