Sertraline → Sertraline Hydrochloride

HRID 1393719Notes

Reaction equation

HRID 1393719 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>C(O)CCC>[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:19]

Participants

3

Reactant 1

HCID 68617Sertraline

Product 1

HCID 63009Sertraline HydrochlorideYield 70%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Sertraline base (27 kg) was dissolved in 105 kg of n-butanol. The solution was treated for 1 hour with 1 kg carbon at 40 to 45° C. and filtered and washed with 25 kg n-butanol. The solution was reheated to 40-45° C. and the achieved temperature was kept constant during the gas flow and filtration. Hydrogen chloride gas was added at the rate of 4.5-5 kg/hr for the duration of 1 hour until pH 0.5 or less was reached. Immediately thereafter, the slurry was filtered at 40-45° C. The cake was washed with 25 kg of n-butanol, and dried for about 4 hours at 80° C. The yield was 70% (21.2 kg).

Workup

  1. additionThe solution was treated for 1 hour with 1 kg carbon at 40 to 45° C.
  2. filtrationfiltered
  3. washwashed with 25 kg n-butanol
  4. customwas reheated to 40-45° C.
  5. filtrationthe achieved temperature was kept constant during the gas flow and filtration
  6. additionHydrogen chloride gas was added at the rate of 4.5-5 kg/hr for the duration of 1 hour until pH 0.5 or less
  7. filtrationImmediately thereafter, the slurry was filtered at 40-45° C
  8. washThe cake was washed with 25 kg of n-butanol
  9. customdried for about 4 hours at 80° C

Sources & evidence

ORD record
ord-69c738a996294a12ac1127fec035199f
Source dataset
uspto-grants-2008_03
Patent number
US07345201B2

Reaction notes

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