Piperazine → 1-Tritylpiperazine

HRID 546549Notes

Reaction equation

HRID 546549 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[C:7]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=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 121.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Piperazine (107.5 g, 1.25 mole) was dissolved in DCM (500 ml). Trityl chloride (69.7 g, 0.25 mole) was added to the mixture cooled in an ice bath. After addition, the mixture was kept at room temperature for 30 min. The mixture was washed with water (500 ml, three times). And the organic layer was separated and dried over sodium sulfate. The mixture was concentrated to ca. 100 ml and added to hexane (1 liter). The solid was removed by filtration. The filtrate was evaporated to dryness to give a white solid (ca. 100 g).

Workup

  1. temperaturecooled in an ice bath
  2. additionAfter addition
  3. washThe mixture was washed with water (500 ml, three times)
  4. customAnd the organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationThe mixture was concentrated to ca. 100 ml
  7. additionadded to hexane (1 liter)
  8. customThe solid was removed by filtration
  9. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-b6d03e62392c4ac79a1f270754c39b21
Source dataset
uspto-grants-2011_05
Patent number
US07935816B2

Reaction notes

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