(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;2-hydroxy-2-phenylacetate → Sertraline Hydrochloride

HRID 2182838Notes

Reaction equation

HRID 2182838 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-])(=O)C(C1C=CC=CC=1)O>CCCCO>[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 131718189(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;2-hydroxy-2-phenylacetate

Product 1

HCID 63009Sertraline Hydrochloride

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Sertraline mandelate (20 g) in n-BuOH (400 ml) was heated to 60° C. A slurry was obtained. HC1 (g) was bubbled through the mixture and complete dissolution was observed. When the solution pH was ˜0.5, the solution was cooled and seeded with sertraline hydrochloride Form II. The reaction mixture was srirred at room temperature over night and a solid was filtered and washed with n-BuOH. The solid was dried to afford sertraline hydrochloride Form II (7.21 g).

Workup

  1. customA slurry was obtained
  2. customHC1 (g) was bubbled through the mixture and complete dissolution
  3. temperatureWhen the solution pH was ˜0.5, the solution was cooled
  4. waitThe reaction mixture was srirred at room temperature over night
  5. filtrationa solid was filtered
  6. washwashed with n-BuOH
  7. customThe solid was dried

Sources & evidence

ORD record
ord-c6f15d52ecc142f39aeeae18292d14bf
Source dataset
uspto-grants-2005_05
Patent number
US06897340B2

Reaction notes

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