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

HRID 1909007Notes

Reaction equation

HRID 1909007 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10](=O)[CH3:11])[C:4]=2[N:3]=[CH:2]1.[CH3:13][NH2:14].Cl.O1CCOCC1.[BH4-].[Na+]>CO>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH:10]([NH:14][CH3:13])[CH3:11])[C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 312751,4-DioxaneHCID 4311764Sodium borohydrideHCID 194259571-(1H-Benzo[d]imidazol-4-yl)ethanone

Product 1

HCID 67286529[1-(1H-benzoimidazol-4-yl)-ethyl]-methyl-amineYield 58.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

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).

Workup

  1. stirringstirred for 1 hour
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-09573f3fb2a344cf8e09b9f36d8b679d
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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