Tetrahydrofuran → HCID 178511612, compound

HRID 22937

Reaction equation

HRID 22937 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7](Cl)=[N:8][CH:9]=1)([O-:3])=[O:2].[C@H:11]1([NH2:18])[CH2:16][CH2:15][C@H:14]([NH2:17])[CH2:13][CH2:12]1.O1CCCC1>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:17][C@H:14]2[CH2:15][CH2:16][C@H:11]([NH2:18])[CH2:12][CH2:13]2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 783082-Chloro-5-nitropyridineHCID 178511674HCID 178511674, compound

Product 1

HCID 178511612HCID 178511612, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-nitro-2-chloropyridine (2.50 g) and trans-1,4-cyclohexanediamine (5.40 g) in ethanol (15 ml)-tetrahydrofuran (10 ml) was stirred at room temperature for 5 days. The precipitates were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent: chloroform-methanol-concentrated aqueous ammonia (20:4:1)) and crystallized from ethyl acetate to obtain N-(5-nitro-2-pyridyl)-trans-1,4-cyclohexanediamine (Reference Example 3-1 in Table 5).

Workup

  1. customThe precipitates were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (solvent: chloroform-methanol-concentrated aqueous ammonia (20:4:1))
  4. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c736fbffea7a41fb8eec7294aa7c060f
Source dataset
uspto-grants-2005_02
Patent number
US06849622B2

Linked notes

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