1-[2-(Benzimidazol-2-ylthio)ethyl]-4-tert-butoxycarbonyl piperazine → 1-[2-(Benzimidazol-2-ylthio)ethyl]piperazine

HRID 1350552Notes

Reaction equation

HRID 1350552 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1>FC(F)(F)C(O)=O>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

3

Reactant 1

HCID 230848911-[2-(Benzimidazol-2-ylthio)ethyl]-4-tert-butoxycarbonyl piperazine

Product 1

HCID 99617871-[2-(Benzimidazol-2-ylthio)ethyl]piperazineYield 152.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-[2-(benzimidazol-2-ylthio)ethyl]-4-tert-butoxycarbonyl piperazine (13.83 g, 38.15 mmol) was dissolved in trifluoroacetic acid (75 mL) in an ice bath, and the mixture was stirred at the same temperature for 30 minutes, and after elevating the temperature to room temperature, the mixture was stirred for another 40 minutes. The reaction solution was concentrated under reduced pressure, and the resulting crystals were recrystallized from methanol-diethyether to give 15.24 g of 1-[2-(benzimidazole-2-ylthio)ethyl]piperazine.3 trifluoroacetate (66%) as pale yellow powdery crystals.

Workup

  1. customto room temperature
  2. stirringthe mixture was stirred for another 40 minutes
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customthe resulting crystals were recrystallized from methanol-diethyether

Sources & evidence

ORD record
ord-ff7466892d6a4001bbaba27e64901016
Source dataset
uspto-grants-2007_05
Patent number
US07214796B2

Reaction notes

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