Ethylenediamine → N-[1-(1-methyl-1H-pyrazol-4-yl)ethyl]ethane-1,2-diamine

HRID 420850Notes

Reaction equation

HRID 420850 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](=O)[CH3:8])[CH:4]=[N:3]1.[CH2:10]([NH2:13])[CH2:11][NH2:12].C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.O1CCCC1.C(O)(=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]([NH:12][CH2:11][CH2:10][NH2:13])[CH3:8])[CH:4]=[N:3]1

Participants

8

Reactant 4

HCID 3301EthylenediamineHCID 516892Sodium BicarbonateHCID 35969391-(1-methyl-1H-pyrazol-4-yl)ethan-1-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 14009898N-[1-(1-methyl-1H-pyrazol-4-yl)ethyl]ethane-1,2-diamineYield 48.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(1-Methyl-1H-pyrazol-4-yl)-ethanone (250 mg) and ethylenediamine (362 mg) were dissolved in methanol (10 ml), the solution was added with acetic acid (1.21 g) and sodium cyanoborohydride (189 mg), and the mixture was stirred at room temperature for 48 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and tetrahydrofuran, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=10:1:0.1) to obtain the title compound (163 mg).

Workup

  1. customthe layers were separated
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=10:1:0.1)

Sources & evidence

ORD record
ord-c448b2dc18304b66a020f37dce9cbb5a
Source dataset
uspto-grants-2012_01
Patent number
US08097708B2

Reaction notes

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