Cyclopropylamine → Ethyl 4-[6-(cyclopropylamino)-3-nitro-2-pyridinyl]-1-piperazinecarboxylate

HRID 620871Notes

Reaction equation

HRID 620871 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]2)[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1.[N:22]12[CH2:32][CH2:31][CH2:30]N=C1CCCCC2.C1(N)CC1>C(O)C>[CH:32]1([NH:22][C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]3)[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=2)[CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13076363Ethyl 4-(6-chloro-3-nitropyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 13565851Ethyl 4-[6-(cyclopropylamino)-3-nitro-2-pyridinyl]-1-piperazinecarboxylateYield 47.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 126.0 g (0.4 mole) of 4-(6-chloro3-nitro-2-pyridinyl)-1-piperazinecarboxylic acid, ethyl ester (prepared as described in European Patent Publication No. 9425), 76.1 g (0.5 mole) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 28.6 g (0.5 mole) of cyclopropylamine and 500 ml of absolute ethanol was stirred at room temperature for 48 hours. The solution was then heated at reflux for four hours and concentrated in vacuo. The residue was partitioned between chloroform and water. The chloroform layer was dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with ether to give 64.0 g of the title compound, mp 100°-103° C.

Workup

  1. temperatureThe solution was then heated
  2. temperatureat reflux for four hours
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between chloroform and water
  5. dry with materialThe chloroform layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-6ae04bde1874450eb0029446216a3b88
Source dataset
uspto-grants-1989_04
Patent number
US04822801

Reaction notes

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