Sodium Hydroxide → 1-Phenylpiperazine

HRID 1405443Notes

Reaction equation

HRID 1405443 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15316568tert-Butyl 4-phenylpiperazine-1-carboxylate

Product 1

HCID 70961-PhenylpiperazineYield 97%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Conditions

Temperature
30 °C

Procedure

A solution of t-butyl 4-phenylpiperazine-1-carboxylate (500 mg, 1.91 mmol, 1.00 equiv) in DCM/CF3COOH (10/3 mL) was placed in a 50-mL round bottom flask and stirred for 1 h at 30° C. in an oil bath. The pH value of the solution was adjusted to 9 with aqueous sodium hydroxide (1 M), and the solution was extracted with 3×10 mL of dichloromethane, the organic layers combined and dried over anhydrous sodium sulfate. Solids were removed via filtration, and the resulting solution concentrated under vacuum yielding 300 mg (97%) of 1-phenylpiperazine as yellow oil.

Workup

  1. extractionthe solution was extracted with 3×10 mL of dichloromethane
  2. dry with materialdried over anhydrous sodium sulfate
  3. customSolids were removed via filtration
  4. concentrationthe resulting solution concentrated under vacuum

Sources & evidence

ORD record
ord-f209083cdee8451a88bc126b3b9a0b8d
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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