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

HRID 1818837Notes

Reaction equation

HRID 1818837 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][N:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)[S:10]2(=[O:34])=[O:33])[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][N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[S:10]2(=[O:33])=[O:34])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68709692tert-butyl 4-{2-[3-(3,4-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]ethyl}piperazine-1-carboxylate

Product 1

HCID 687138131-(3,4-Difluorophenyl)-3-(2-piperazin-1-ylethyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxideYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 4-{2-[3-(3,4-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]ethyl}piperazine-1-carboxylate (0.34 g, 0.69 mmol) in dichloromethane (5 mL) was treated with hydrogen chloride (2.0 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-(2-piperazin-1-ylethyl)-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (0.2 g, 74%) as a white solid:

Workup

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

Sources & evidence

ORD record
ord-58ebb1f467134242bc132baf8d20e07c
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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