Sulfuric Acid → 1-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-N-methyl-1H-benzimidazol-5-amine

HRID 1796490Notes

Reaction equation

HRID 1796490 reaction equation
CO[C:3](=O)[NH:4][C:5]1[CH:27]=[CH:26][C:8]2[N:9]([CH2:22][CH:23]3[CH2:25][CH2:24]3)[C:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=3)=[N:11][C:7]=2[CH:6]=1.[AlH3].OS(O)(=O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1>C1COCC1>[CH:23]1([CH2:22][N:9]2[C:8]3[CH:26]=[CH:27][C:5]([NH:4][CH3:3])=[CH:6][C:7]=3[N:11]=[C:10]2[CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH3:21])=[CH:17][CH:18]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14488Aluminum hydrideHCID 68718528lithium aluminium hydride THFHCID 86605606methyl [1-(cyclopropylmethyl)-2-[(4-ethoxyphenyl)methyl]-1H-benzimidazol-5-yl]carbamate

Product 1

HCID 221812881-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-N-methyl-1H-benzimidazol-5-amineYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl-1-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-1H-benzimidazol-5-ylcarbamate (1.65 g, 4.35 mmol) was added portionwise to a cold (0° C.) solution of AlH3 (˜0.3 M), which was freshly prepared by adding dropwise conc. H2SO4 (0.80 g, 8.10 mmol) to 1 M LiAlH4 THF solution (16 ml, 16 mmol) in THF (30 mL) at 0° C. The reaction mixture was stirred at room temperature overnight, and subsequently quenched carefully by adding EtOAc (5 mL), H2O (3 mL) and Et2O (100 mL), and then Na2SO4.5H2O (10 g). The reaction mixture was stirred until a clear solution was produced, and the solid was filtered off. The filtrate was dried over Na2SO4 and concentrated in vacuo to afford desired compound (1.21 g). The crude product was used for next step without further purification.

Workup

  1. customwas freshly prepared
  2. customsubsequently quenched carefully
  3. additionby adding EtOAc (5 mL), H2O (3 mL) and Et2O (100 mL)
  4. stirringThe reaction mixture was stirred until a clear solution
  5. customwas produced
  6. filtrationthe solid was filtered off
  7. dry with materialThe filtrate was dried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d12410b4b944866b07a9af4bd346759
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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