Isoamylamine → HCID 15546371, compound

HRID 649892Notes

Reaction equation

HRID 649892 reaction equation
Cl[CH2:2][C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[N:4]=1.[CH2:20]([NH2:25])[CH2:21][CH:22]([CH3:24])[CH3:23]>C(#N)C>[CH3:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][N:7]1[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[N:4]=[C:3]1[CH2:2][NH:25][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 7894IsoamylamineHCID 15546370HCID 15546370, compound

Product 1

HCID 15546371HCID 15546371, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5.4 mmole 2-(chloromethyl)-1-[(2-methylphenyl)methyl]benzimidazole in 20 mL of dry Acetonitrile is treated with 10 mL of isoamylamine for 16 hr at room temperature. The solvent is removed in vacuo and the residue is partitioned between 30 mL of ethyl acetate and 10 mL of 1 N NaOH. The ethyl acetate layer is dried over anhydrous Na2SO4 and solvent removed in vacuo to afford 1.6 g 92% ({1-[(2-methylphenyl)methyl]benzimidazol-2-yl}methyl) (3-methylbutyl)amine. 2,4-dimethoxybenzoylchloride 1.5 eq is treated with 1.0 eq of ({1-[(2-methylphenyl)methyl]benzimidazol-2-yl}methyl) (3-methylbutyl)amine in dichloromethane at room temperature for 1 hr. The reaction is quenched with 1 N NaOH and partitioned between dichloromethane and water. The organic layer is dried with Na2SO4 and the solvent removed in vacuo. The residue is chromatographed (SiO2) with ethyl acetate to afford 95% of (2,4-dimethoxyphenyl)-N-({1-[(2-methylphenyl)methyl]benzimidazol-2-yl}methyl)-N-(3-methylbutyl)carboxamide (Compound 1). Mass Spec M+ 486.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between 30 mL of ethyl acetate and 10 mL of 1 N NaOH
  3. dry with materialThe ethyl acetate layer is dried over anhydrous Na2SO4 and solvent
  4. customremoved in vacuo

Sources & evidence

ORD record
ord-f5063c017a28479e94ed1ae5a2e5a7d6
Source dataset
uspto-grants-2001_08
Patent number
US06271241B1

Reaction notes

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