Vortioxetine hydrobromide → Vortioxetine

HRID 1909085Notes

Reaction equation

Br.[CH3:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C(O)(C)C.O>[CH3:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1

Participants

Conditions

Temperature: 20 °C

Procedure

1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine-HBr (33.1 Kg) in a mixture of isopropanol (412 L) and water (18 L) was heated to reflux. The solution was cooled to 20° C. and isopropanol solvate of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine was isolated by filtration and washed with isopropanol (82 L). The wet filter cake was dissolved in a mixture of isopropanol (353 L) and water (17 L) at reflux. The solution was cooled to 20° C. and isopropanol solvate of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine was isolated by filtration and washed with isopropanol (74 L). The wet filter cake was dissolved in a mixture of toluene (132 L) and water (13 L) at 80° C. and blank filtered. Water and isopropanol were distilled out of the reactor (55 L), distillation was stopped when distillate reached 102° C. Water (7 L) was then added and the solution was cooled to 20° C. slowly. 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine-HBr was isolated by filtration, filter cake washed with toluene (77 L) and dried. The amounts of impurities were less than 0.05% of compound 1, less than 0.015% of compound 2 and less than 0.05% of compound 3.

Workup

temperaturewas heated to reflux

Sources & evidence

ORD record: ord-10c2c5d6b53844508d8bfeca3d4c1cc2
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598348B2

Reaction notes

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