Sodium Hydroxide → 1-(2-Pyridyl)piperazine

HRID 1405431Notes

Reaction equation

HRID 1405431 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]1.[OH-].[Na+]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11975669tert-Butyl 4-(pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 944591-(2-Pyridyl)piperazineYield 97%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Conditions

Temperature
30 °C

Procedure

A solution of t-butyl 4-(pyridin-2-yl)piperazine-1-carboxylate (500 mg, 1.90 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 (1M), then extracted with 3×10 mL of dichloromethane. The organic layers combined, dried over anhydrous sodium sulfate, and filtered to remove solids. The resulting solution was concentrated under vacuum, yielding 300 mg (97%) of 1-(pyridin-2-yl)piperazine as yellow oil.

Workup

  1. extractionextracted with 3×10 mL of dichloromethane
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customto remove solids
  5. concentrationThe resulting solution was concentrated under vacuum

Sources & evidence

ORD record
ord-86fafc665c724fc19a4d0fe4a78173af
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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