Hydrochloric Acid → HCID 23512747, compound

HRID 2304904Notes

Reaction equation

HRID 2304904 reaction equation
C([O:3][C:4]([CH:6]1[C:14]2[N:13]=[CH:12][N:11]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]=2[CH2:9][CH2:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].Cl>C1COCC1.O>[OH:3][CH2:4][CH:6]1[C:14]2[N:13]=[CH:12][N:11]([C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:10]=2[CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22961978HCID 22961978, compound

Product 1

HCID 23512747HCID 23512747, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazole-4-carboxylic acid ethyl ester (14.0 g, 32 mmol) in THF (100 ml) was added lithium aluminium hydride (24 ml, 1 mol/L in THF, 24 mmol). The mixture was stirred at 20° C. for 45 min, and water (3.5 ml) and sodium hydroxide (3.5 ml, 4 mol/L in water) were carefully added. Water (14 ml) and concentrated aqueous hydrochloric acid (1.13 ml) were added, and the mixture was filtered and concentrated under reduced pressure. The residue was re-dissolved in ethyl acetate (150 ml), dried (magnesium sulphate), filtered, and kept at 20° C. overnight. Filtration yielded 7.0 g (55%) of 4-hydroxymethyl-1-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazole as a colourless solid.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was re-dissolved in ethyl acetate (150 ml)
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. waitkept at 20° C. overnight
  7. filtrationFiltration

Sources & evidence

ORD record
ord-179fadc375d74e9a95bb6e14c7af22b8
Source dataset
uspto-grants-2002_08
Patent number
US06437147B1

Reaction notes

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