1-Ethylpiperazine → Ethyl-4-(4-nitro-pyridin-2-yl)-piperazine

HRID 272526Notes

Reaction equation

HRID 272526 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[CH2:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH3:12].C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[CH2:11]([N:13]1[CH2:18][CH2:17][N:16]([C:2]2[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N:3]=2)[CH2:15][CH2:14]1)[CH3:12]

Participants

6

Reactant 3

HCID 791961-EthylpiperazineHCID 81531DiisopropylethylamineHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 68942070Ethyl-4-(4-nitro-pyridin-2-yl)-piperazineYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2 g (13 mmol) 2-chloro-4-nitropyridine, 1.73 g (15 mmol) 1-ethyl-piperazine and 0.81 g (6 mmol) N,N-diisopropylethylamine (DIPEA) in 19 ml DMF and 20 ml water was heated to 100° C. for 24 h. The precipitate was filtered off and washed three times with 4 ml of water and dried for 24 h under vacuum to yield 2.03 g (68%) of the title compound as yellow oil (m/e): 236.7 (MH+; 100%).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed three times with 4 ml of water
  3. customdried for 24 h under vacuum

Sources & evidence

ORD record
ord-f60116fa59b14bbbaff3d57bd4ecbb69
Source dataset
uspto-grants-2008_11
Patent number
US07456175B2

Reaction notes

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