Hydrochloric Acid → 1-(3,4-Difluorophenyl)-3-(3-piperazin-1-ylpropyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

HRID 1818839Notes

Reaction equation

HRID 1818839 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)[S:10]2(=[O:35])=[O:34])[CH:5]=[CH:6][C:7]=1[F:8].Cl>ClCCl.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[S:10]2(=[O:34])=[O:35])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68709886tert-butyl 4-{3-[3-(3,4-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]propyl}piperazine-1-carboxylate

Product 1

HCID 578862471-(3,4-Difluorophenyl)-3-(3-piperazin-1-ylpropyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxideYield 89.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 4-{3-[3-(3,4-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]propyl}piperazine-1-carboxylate (0.16 g, 0.3 mmol) in dichloromethane (10 mL) was treated with hydrogen chloride (6.0 mL of a 4 M solution in dioxane), resulting in a white precipitate that was evaporated and dried under vacuum to provided 1-(3,4-difluorophenyl)-3-(3-piperazin-1-ylpropyl)-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (0.11 g, 81%) as a white solid:

Workup

  1. customresulting in a white precipitate that
  2. customwas evaporated
  3. customdried under vacuum

Sources & evidence

ORD record
ord-c7982fd9696c4c989d14e9a569a26371
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

Loading…