HCID 18687551, compound → HCID 86755698, compound

HRID 1872769Notes

Reaction equation

HRID 1872769 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[C:5]([N:7]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9][C@@H:8]1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:6].Cl[C:26]1[N:30]([CH2:31][C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)[C:29]2[CH:37]=[CH:38][CH:39]=[CH:40][C:28]=2[N:27]=1>C(Cl)Cl.[Cu]>[CH3:24][C:22]1[CH:21]=[C:4]([CH:3]=[C:2]([CH3:1])[CH:23]=1)[C:5]([N:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:26]2[N:30]([CH2:31][C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[C:29]3[CH:37]=[CH:38][CH:39]=[CH:40][C:28]=3[N:27]=2)[CH2:9][C@@H:8]1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:6]

Participants

5

Reactant 2

HCID 18687551HCID 18687551, compoundHCID 86755699HCID 86755699, compound

Product 1

HCID 86755698HCID 86755698, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6344DichloromethaneSolvent

Procedure

(±)-cis-1-(3,5-dimethylbenzoyl)-2-(phenylmethyl)-4-piperidinamine (1.2 g), 2-chloro-1-(2-thienylmethyl)-1H-benzimidazole (2.24 g) and copper (0.6 g) were stirred at 150° C. for 5 hours. The mixture was taken up in CH2Cl2 and filtered. The filtrate was washed with diluted NH4OH and stirred. The organic layer was separated, dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 97/3). The pure fractions were collected and the solvent evaporated. The residue was crystallized from CH3CN, yielding 1.87 g (35%) of (±)-cis-1-(3,5-dimethylbenzoyl)-2-(phenylmethyl)-N-[1-(2-thienylmethyl)-1H-benzimidazol-2-yl]-4-piperidinamine (comp. 76; mp. 201.4° C.).

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with diluted NH4OH
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 97/3)
  8. customThe pure fractions were collected
  9. customthe solvent evaporated
  10. customThe residue was crystallized from CH3CN

Sources & evidence

ORD record
ord-352784737fd849798d02d974e6d60cca
Source dataset
uspto-grants-2000_08
Patent number
US06110939

Reaction notes

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