Water → 1-Tritylpiperazine

HRID 80303Notes

Reaction equation

HRID 80303 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7]1([C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)Cl)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>CN(C)C=O>[C:7]1([C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 6456Trityl chloride

Product 1

HCID 114729311-TritylpiperazineYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Piperazine (1.00 g, 11.6 mmol) (Wako Pure Chemical Industries, Ltd.) was dissolved in N,N-dimethylformamide (25 mL) (Wako Pure Chemical Industries, Ltd.), and triphenylchloromethane (0.65 g, 2.33 mmol) (Wako Pure Chemical Industries, Ltd.) was added little by little, and the mixture was stirred at room temperature overnight. Water was poured into the reaction solution, and mixture was extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.). The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.):methanol (Wako Pure Chemical Industries, Ltd.)=9:1 as an eluent). The residue was dissolved in ethyl acetate and a saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.), and the mixture was shaken, followed by separation of the organic layer. The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and then the solvent was distilled off under reduced pressure, to thereby obtain the title compound (0.76 g, 99% yield).

Workup

  1. extractionwas extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. stirringa saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.), and the mixture was shaken
  6. customfollowed by separation of the organic layer
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-694a3a2c6f0642f597aa95811555848e
Source dataset
uspto-grants-2014_09
Patent number
US08846012B2

Reaction notes

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