Hydrochloric Acid → Sertraline Hydrochloride

HRID 1794663Notes

Reaction equation

HRID 1794663 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].O>C(O)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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68617Sertraline

Product 1

HCID 63009Sertraline HydrochlorideYield 94.65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sertraline base (3 g) was dissolved in 10 mL absolute ethanol at 40° C. The solution was heated to 50–60° C. and concentrated hydrochloric acid 32% (1.2 mL) was added until pH ˜1.3 was reached. Water (12 mL) was added. The resulting clear solution was concentrated to half its volume and was allowed to cool naturally to room temperature. The solid was isolated by filtration, washed with water and dried overnight at 50–60° C., yielding 3.18 g (94.65%) sertraline hydrochloride Form V.

Workup

  1. temperatureThe solution was heated to 50–60° C.
  2. concentrationThe resulting clear solution was concentrated to half its volume
  3. customThe solid was isolated by filtration
  4. washwashed with water
  5. customdried overnight at 50–60° C.

Sources & evidence

ORD record
ord-c1ab98e7c2be4168af18062f83d69130
Source dataset
uspto-grants-2006_04
Patent number
US07022881B2

Reaction notes

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