2-chloro-1-(2-ethoxyethyl)-1H-benzimidazole → HCID 67672022, compound

HRID 1872760Notes

Reaction equation

HRID 1872760 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:4]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3]1.[CH2:22]([O:24][CH2:25][CH2:26][N:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1Cl)[CH3:23]>C(Cl)Cl.[Cu]>[CH2:22]([O:24][CH2:25][CH2:26][N:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[NH:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:4]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:3]1)[CH3:23]

Participants

5

Reactant 2

HCID 104893562-chloro-1-(2-ethoxyethyl)-1H-benzimidazoleHCID 86755688HCID 86755688, compound

Product 1

HCID 67672022HCID 67672022, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6344DichloromethaneSolvent

Procedure

(±)-1,1-dimethylethyl trans-4-amino-2-(phenylmethyl)-1-piperidinecarboxylate (5 g), 1-(2-ethoxyethyl)-2-chloro-1H-benzimidazole (4.5 g) and copper (1.28 g) were stirred at 150° C. for 4 hours. The mixture was taken up in CH2Cl2 and filtered. The filtrate was washed with water/NH3. The organic layer was dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 98/2). The pure fractions were collected and the solvent evaporated, yielding 6 g (73.7%) of (±)-1,1-dimethylethyl trans-4-[[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]amino]-2-(phenylmethyl)-1-piperidine-carboxylate (interm. 6).

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water/NH3
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 98/2)
  7. customThe pure fractions were collected
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-e1ac21f556ca4ebe9e97a5e8b81b0298
Source dataset
uspto-grants-2000_08
Patent number
US06110939

Reaction notes

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