Hydrochloric Acid → (3H-Imidazol-4-ylmethyl)-(3-methoxy-phenyl)-methyl-amine

HRID 2043347Notes

Reaction equation

HRID 2043347 reaction equation
[N:1]1[CH:5]=[C:4]([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[NH:3][CH:2]=1.C=O.[C:18]([BH3-])#N.[Na+].Cl>C(#N)C>[N:1]1[CH:5]=[C:4]([CH2:6][N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[CH3:18])[NH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59728243(3H-Imidazol-4-ylmethyl)-(3-methoxy-phenyl)-amine

Product 1

HCID 59728031(3H-Imidazol-4-ylmethyl)-(3-methoxy-phenyl)-methyl-amineYield 75.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3H-Imidazol-4-ylmethyl)-(3-methoxy-phenyl)-amine (0.070 g, 0.34 mmol) was dissolved in acetonitrile (10 ml). Then formaldehyde (0.0.06 ml, 0.86 mmol, 37% aqueous solution) and sodium cyanoborohydride (0.065 g, 1.03 mmol) were added and the reaction mixture was allowed to stir at room temperature for 10 minutes. The reaction mixture was then acidified to pH 2-3 by dropwise addition of concentrated hydrochloric acid whereupon precipitation occurred. The mixture was stirred for a further 1 h at room temperature before being concentrated in vacuo. The residue was taken up in ethyl acetate, washed with 1 M aqueous sodium hydroxide solution and the organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified using flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: methanol/dichloromethane gradient) to yield a white solid (0.056 g, 75%); MS (ISP): 218.3 ([M+H]+).

Workup

  1. stirringThe mixture was stirred for a further 1 h at room temperature
  2. concentrationbefore being concentrated in vacuo
  3. washwashed with 1 M aqueous sodium hydroxide solution
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-7c518e62435f4adfa739e08d309e272c
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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