Allylamine → HCID 3229441, compound

HRID 1009869Notes

Reaction equation

HRID 1009869 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[CH2:5]([N:7]([CH2:10][CH3:11])[CH2:8][CH3:9])[CH3:6].ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:14].C[N:26]1[CH2:31]CNCC1>C(Cl)(Cl)Cl>[CH2:1]([NH:4][C:6]([CH2:5][N:7]1[CH2:10][CH2:11][N:26]([CH3:31])[CH2:9][CH2:8]1)=[O:14])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 7853AllylamineHCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 3229441HCID 3229441, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a chloroform solution (70 mL) of allylamine (400 mg, 7.00 mmol) were added triethylamine (1.31 mL, 9.45 mmol) and 4-nitrophenyl chloroformate (1.62 g, 8.06 mmol), and the mixture was stirred overnight at room temperature. To this reaction solution was added 1-methylpiperazine (771 mg, 7.70 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was evaporated under reduced pressure. To thus obtained residue was added ethyl acetate, and precipitated insoluble matter was filtered off. The filtrate was concentrated, and thus obtained residue was purified with NH type silica gel column chromatography (hexane:ethyl acetate=5:1, ethyl acetate), and silica gel column chromatography (ethyl acetate, chloroform:methanol=20:1 to 5:1) to obtain the title compound (1.38 g, quant.) as a colorless powder.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe reaction solution was evaporated under reduced pressure
  3. additionTo thus obtained residue was added ethyl acetate
  4. customprecipitated insoluble matter
  5. filtrationwas filtered off
  6. concentrationThe filtrate was concentrated
  7. customthus obtained residue was purified with NH type silica gel column chromatography (hexane:ethyl acetate=5:1, ethyl acetate), and silica gel column chromatography (ethyl acetate, chloroform:methanol=20:1 to 5:1)

Sources & evidence

ORD record
ord-350ea7740897417db8860eb656d23b66
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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