Ammonium Acetate → 4-(1H-Benzo[d]imidazol-1-yl)butan-2-amine

HRID 1902457Notes

Reaction equation

HRID 1902457 reaction equation
O=[C:2]([CH3:14])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:21].[Na+]>CO>[CH3:14][CH:2]([NH2:21])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 132678772-Butanone, 4-(1H-benzimidazol-1-yl)-

Product 1

HCID 132678794-(1H-Benzo[d]imidazol-1-yl)butan-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7.0 grams of 1-(3-oxobutyl)-1H-benzimidazole, 28.7 grams of ammonium acetate and 1.6 grams of sodium cyanoborohydride in 100 ml. of methanol was stirred at room temperature for about 24 hours. The mixture was then acidified with about 40 ml. of concentrated hydrochloric acid and the solvent was evaporated. The residue was dissolved in 150 ml. of water and the aqueous solution was extracted first with ether and then it was made alkaline (pH greater than 10) with solid potassium hydroxide. The alkaline solution was extracted with several portions of methylene chloride and the organic extracts were combined, washed with water and dried over magnesium sulfate and the methylene chloride was evaporated. The residue was chromatographed on a silica gel column packed in acetonitrile and eluted with acetonitrile and acetonitrile containing increasing percentages of methanol. The fractions containing the desired product, as determined by thin-layer chromatography, were combined and the solvent evaporated to give α-methyl-1H-benzimidazole-1-propanamine as an oil.

Workup

  1. customof concentrated hydrochloric acid and the solvent was evaporated
  2. dissolutionThe residue was dissolved in 150 ml
  3. extractionof water and the aqueous solution was extracted first with ether
  4. extractionThe alkaline solution was extracted with several portions of methylene chloride
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe methylene chloride was evaporated
  8. customThe residue was chromatographed on a silica gel column
  9. washeluted with acetonitrile and acetonitrile containing
  10. temperatureincreasing percentages of methanol
  11. additionThe fractions containing the desired product
  12. customthe solvent evaporated

Sources & evidence

ORD record
ord-b57abd8158d54a12ae3f3a2f7c6d1ecc
Source dataset
uspto-grants-1982_12
Patent number
US04363808

Reaction notes

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