Diethyl Ether → 1-[2-(5,6-Difluorobenzimidazol-2-ylthio)ethyl]piperazine tris(trifluoroacetic acid) salt

HRID 1354251Notes

Reaction equation

HRID 1354251 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16][C:17]2[NH:18][C:19]3[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:20]=3[N:21]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31].CCOCC>CCCCCC>[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31].[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31].[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31].[F:27][C:23]1[C:24]([F:26])=[CH:25][C:19]2[N:18]=[C:17]([S:16][CH2:15][CH2:14][N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[NH:21][C:20]=2[CH:22]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 117110271-Tert-butoxycarbonyl-4-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]piperazine

Product 1

HCID 230924391-[2-(5,6-Difluorobenzimidazol-2-ylthio)ethyl]piperazine tris(trifluoroacetic acid) saltYield 82%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Under stirring in an ice-bath, 1-tert-butoxycarbonyl-4-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]piperazine (7.26 g, 18.22 mmol) was added to trifluoroacetic acid (50 mL) over 15 minutes and dissolved. After the mixture had been stirred for ten minutes under cooling with ice, ether (100 mL) and hexane (100 mL) were added thereto, and the formed crystals were collected through filtration. The crystals were recrystallized from ethanol-ether, to thereby yield 1-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]piperazine tris(trifluoroacetic acid) salt (9.58 g, yield 82%) as a pale yellow powder.

Workup

  1. dissolutiondissolved
  2. stirringAfter the mixture had been stirred for ten minutes
  3. additionwere added
  4. filtrationthe formed crystals were collected through filtration
  5. customThe crystals were recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-8c4616f7293547f581a923d7fe4e93cd
Source dataset
uspto-grants-2007_05
Patent number
US07223764B2

Reaction notes

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