Piperazine → 1-Tritylpiperazine

HRID 482939Notes

Reaction equation

HRID 482939 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7]1([C:13](Cl)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCCC1>[C:13]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 6456Trityl chloride

Product 1

HCID 114729311-TritylpiperazineYield 23.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of piperazine (25.9 g, 0.30 mol) in tetrahydrofuran (300 ml) at 0° C. was added triphenylmethyl chloride (27.9 g, 0.10 mol). The reaction was stirred for 48 hours at room temperature. The product was extracted from aqueous sodium carbonate with three portions of ether. The combined organic layers were washed with three portions of water, dried with sodium sulfate, and the volatiles were then evaporated. The residue was subjected to chromatography on silica (LPS-1) (eluting with 90:10:4 ether/acetonitrile/triethylamine) to yield 7.62 g of N-tritylpiperazine.

Workup

  1. extractionThe product was extracted from aqueous sodium carbonate with three portions of ether
  2. washThe combined organic layers were washed with three portions of water
  3. dry with materialdried with sodium sulfate
  4. customthe volatiles were then evaporated

Sources & evidence

ORD record
ord-36d51ed950354c24a52cd00551ba5d02
Source dataset
uspto-grants-1986_03
Patent number
US04576749

Reaction notes

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