Trifluoroacetic acid → 1-(5-Nitropyridin-2-yl)piperazine

HRID 1820623Notes

Reaction equation

HRID 1820623 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[N:15][CH:16]=1)([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 16217943tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 29287991-(5-Nitropyridin-2-yl)piperazineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(5-Nitropyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (3.08 g, 10 mmol) was treated with 15% TFA in dichloromethane (50 mL) at 25° C. for 1 h. The solution was concentrated in vacuo to provide 1-(5-nitropyridin-2-yl)piperazine as a brown solid (2.0 g, 96% yield over two steps). MS (ES+) m/z 209.4 (M+1).

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-09853a070693464e97ba4a0673cdb209
Source dataset
uspto-grants-2009_10
Patent number
US07605161B2

Reaction notes

Loading…