Water → HCID 21273569, compound

HRID 1382934Notes

Reaction equation

HRID 1382934 reaction equation
[CH3:1][NH:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[K+]>O1CCCC1>[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[NH:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21273507HCID 21273507, compound

Product 1

HCID 21273569HCID 21273569, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.98 g (0.0075 mol) of N-methyl-p-[(2-benzimidazolyl)methyl]benzamide are added portionwise to a stirred suspension of 0.58 g (0.0075 mol) of lithium aluminium hydride in 40 ml of tetrahydrofuran and subsequently heated to reflux for 4 hours. At 5°-10° there are added dropwise 1.5 ml of water, then 2.3 ml of a 10% solution of potassium hydroxide and again 1.5 ml of water. The precipitate is filtered off and boiled three times with 20 ml of tetrahydrofuran each time. The combined filtrates are washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue is chromatographed on 150 g of silica gel with methanol/concentrated ammonium hydroxide (100:1) as the elution agent. There are obtained 1.58 g (84%) of 2-[4-[(methylamino)methyl]benzyl]benzimidazole, m.p. 157°-160°, as a colourless crystalline powder.

Workup

  1. temperaturesubsequently heated
  2. temperatureto reflux for 4 hours
  3. filtrationThe precipitate is filtered off
  4. washThe combined filtrates are washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue is chromatographed on 150 g of silica gel with methanol/concentrated ammonium hydroxide (100:1) as the elution agent

Sources & evidence

ORD record
ord-638ec12833504d9c9ecf54e2761a1f27
Source dataset
uspto-grants-1989_02
Patent number
US04808605

Reaction notes

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