Imidazole → 3-(1H-Imidazol-1-yl)-2-methylpropan-1-amine

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[C:6](#[N:10])[C:7]([CH3:9])=[CH2:8]>>[N:1]1([CH2:8][CH:7]([CH3:9])[CH2:6][NH2:10])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Reactant 2

HCID 795Imidazole

HCID 31368Methacrylonitrile

Product 1

HCID 139528593-(1H-Imidazol-1-yl)-2-methylpropan-1-amine

Procedure

A mixture of 15.0 g. of imidazole and 25 ml. of methacrylonitrile was heated at reflux temperature for 18 hours and then concentrated to remove the volatile material. The residue was mixed with 150 ml. of ethanol, 75 ml. of ammonium hydroxide and 6 g. of Raney Nickel catalyst and reduced in a Parr hydrogenator under hydrogen pressure until reduction was complete. The catalyst was removed by filtration and the mother liquor was concentrated to remove the solvents. The residual oil was used in reactions without further purification.

Workup

additionA mixture of 15.0 g
temperatureat reflux temperature for 18 hours
concentrationconcentrated
customto remove the volatile material
additionThe residue was mixed with 150 ml
customThe catalyst was removed by filtration
concentrationthe mother liquor was concentrated
customto remove the solvents
customThe residual oil was used in reactions without further purification

Sources & evidence

ORD record: ord-8a5cb7a754324781a6438db3b65fd06d
Source dataset: uspto-grants-1986_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04568687

Reaction notes

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