2-Chloro-5-nitropyridine → 1-Ethyl-4-(5-nitropyridin-2-yl)piperazine

HRID 490077Notes

Reaction equation

HRID 490077 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[CH2:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH3:21]>O.CN(C=O)C>[CH2:20]([N:22]1[CH2:27][CH2:26][N:25]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:24][CH2:23]1)[CH3:21]

Participants

6

Reactant 3

HCID 783082-Chloro-5-nitropyridineHCID 791961-EthylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 28489801-Ethyl-4-(5-nitropyridin-2-yl)piperazineYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2 g (13 mmol) 2-chloro-5-nitro-pyridine and 0.76 g (6 mmol) N,N-diisopropylethylamine in 21 ml water and 4 ml DMF was heated to 80° C. During 2 min 1.73 g (15 mmol) N-ethylpiperazine was added and the mixture was kept for an additional hour at 80° C. The yellow precipitate was filtered off and washed three times with 4 ml water and dried for 16 h under vacuum to yield 2.48 g (83%) of the title compound as yellow crystals. (m/e): 237.1 (MH+; 100%).

Workup

  1. waitthe mixture was kept for an additional hour at 80° C
  2. filtrationThe yellow precipitate was filtered off
  3. washwashed three times with 4 ml water
  4. customdried for 16 h under vacuum

Sources & evidence

ORD record
ord-2fcaaf8ab2504a0ab7b71e85c6a26e7e
Source dataset
uspto-grants-2009_05
Patent number
US07528135B2

Reaction notes

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