Piperazine → N-(3-benzhydroxypropyl)piperazine

HRID 565633Notes

Reaction equation

HRID 565633 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7]1([CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:14][CH2:15][CH2:16][CH2:17]Br)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C.[Na+].[Cl-]>[C:19]1([CH:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:14][CH2:15][CH2:16][CH2:17][N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 143063671-(Diphenylmethoxy)-3-bromopropane

Product 1

HCID 22110970N-(3-benzhydroxypropyl)piperazineYield 99.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 5234Sodium ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

In 20 mL of ethanol was dissolved 20 g of piperazine with heating. Then, a solution of 3-(diphenylmethoxy)propyl bromide (7.0 g) in ethanol (20 mL) was added dropwise and the mixture was stirred at 70° C. for 1 hour. This reaction mixture was diluted with saturated aqueous NaCl and extracted with chloroform. The extract was washed with saturated aqueous NaCl to remove the starting material piperazine, dried over MgSO4, and concentrated under reduced pressure to provide 7.1 g of the title compound. Yield 99%. This product was not further purified but directly submitted to the next reaction.

Workup

  1. temperaturewith heating
  2. extractionextracted with chloroform
  3. washThe extract was washed with saturated aqueous NaCl
  4. customto remove the starting material piperazine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-546818fe66f54360b2ea26b4243be733
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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