Hydrochloric Acid → Sertraline Hydrochloride

HRID 1359610Notes

Reaction equation

HRID 1359610 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

Conditions

Temperature
55 °C

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. concentrationThe resulting clear solution was concentrated to half its volume
  2. temperatureto cool naturally to room temperature
  3. customThe solid was isolated by filtration
  4. washwashed with water
  5. customdried overnight at 50-60° C.

Sources & evidence

ORD record
ord-0a64f80cbfc242d8a3b14b1def354a98
Source dataset
uspto-grants-2003_07
Patent number
US06600073B1

Reaction notes

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