Hydrochloric Acid → [1-(1H-benzoimidazol-4-yl)-ethyl]-methyl-amine

https://huagongshe.com/reaction/1909007

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Methylamine	HCID 6329	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	Sodium borohydride	HCID 4311764	—
Reactant	1-(1H-Benzo[d]imidazol-4-yl)ethanone	HCID 19425957	—
Solvent	Methanol	HCID 887	—
Product	[1-(1H-benzoimidazol-4-yl)-ethyl]-methyl-amine	HCID 67286529	58.5%

Reaction Conditions

Temperature	0 °C

Reaction Steps

A solution of 1-(1H-benzoimidazol-4-yl)ethanone (72 mg, 0.449 mmol), methylamine (2M in THF; 2.25 mL, 4.50 mmol) and HCl in 1,4-dioxane (4M; 0.337 mL, 1.35 mmol) in MeOH (2.7 mL) was stirred at room temperature for 3 days before it was cooled to 0° C. and NaBH4 (20 mg, 0.539 mmol) was added in a single portion. The mixture was stirred at room temperature overnight before it was diluted with MeOH, stirred for 1 hour and concentrated in vacuo. The residue was purified by SiO2 chromatography providing [1-(1H-benzoimidazol-4-yl)-ethyl]-methyl-amine (46 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08598217B2
Source dataset	uspto-grants-2013_12
ORD ID	ord-09573f3fb2a344cf8e09b9f36d8b679d
Source note	uspto-grants-2013_12