Ammonia → Sertraline Hydrochloride

HRID 458230Notes

Reaction equation

HRID 458230 reaction equation
[Cl-:1].[NH4+].O.[CH3:4][NH:5][C@@H:6]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C@H:9]([C:16]2[CH:17]=[CH:18][C:19]([Cl:23])=[C:20]([Cl:22])[CH:21]=2)[CH2:8][CH2:7]1.N>C(O)CC>[CH3:4][NH:5][C@@H:6]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C@H:9]([C:16]2[CH:17]=[CH:18][C:19]([Cl:23])=[C:20]([Cl:22])[CH:21]=2)[CH2:8][CH2:7]1.[ClH:1]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 25517Ammonium ChlorideHCID 68617Sertraline

Product 1

HCID 63009Sertraline HydrochlorideYield 88.1%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Procedure

8.75 g of ammonium chloride are dissolved in 100 ml of n-propanol and 35 ml of water at T=50° C. 50 g of free sertraline base dissolved in 100 ml of n-propanol are added dropwise to the solution thus obtained. It Is heated under reflux and is maintained under agitation under a light nitrogen flow until ammonia is no longer evolved and the pH of the solution becomes slightly acidic. It is cooled to room temperature and is seed crystallized with 0.5 g of sertraline hydrochloride form II. A crystalline solid begins to precipitate and agitation is maintained for 1.5 hours. The solid is filtered, washed and dried under vacuum. 49.3 g of sertraline hydrochloride form II (yield 88%) are obtained.

Workup

  1. customat T=50° C
  2. additionare added dropwise to the solution
  3. customthus obtained
  4. temperatureIt Is heated
  5. temperatureunder reflux
  6. customcrystallized with 0.5 g of sertraline hydrochloride form II
  7. customto precipitate
  8. temperatureagitation is maintained for 1.5 hours
  9. filtrationThe solid is filtered
  10. washwashed
  11. customdried under vacuum

Sources & evidence

ORD record
ord-60eeddb47b5d4521951c5dd90e75b920
Source dataset
uspto-grants-2007_03
Patent number
US07189876B2

Reaction notes

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