Hydrogen chloride-ethyl acetate → 1-[3-(2-Fluorophenyl)-1,2,4-thiadiazol-5-yl]piperazine hydrochloride

HRID 2263241Notes

Reaction equation

HRID 2263241 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([N:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)[S:10][N:9]=1.[ClH:26].C(OCC)(=O)C>CO>[ClH:26].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([N:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)[S:10][N:9]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 68778698Tert-butyl 4-[3-(2-fluorophenyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxylate

Product 1

HCID 687780661-[3-(2-Fluorophenyl)-1,2,4-thiadiazol-5-yl]piperazine hydrochlorideYield 86.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 4-[3-(2-fluorophenyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxylate (5.70 g, 15.6 mmol), 4 N hydrogen chloride/ethyl acetate (200 ml) and methanol (100 ml) was stirred at room temperature for 12 hours. The solvent was distilled off under reduced pressure, and the residue was recrystallized from a mixed solvent of methanol and ether to give 4.31 g (86.5%) of the desired product as a solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was recrystallized from a mixed solvent of methanol and ether

Sources & evidence

ORD record
ord-bcd2566636774cc8ac8de3c5b06f1504
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

Loading…