Isatoic Anhydride → HCID 86755704, compound

HRID 1872772Notes

Reaction equation

HRID 1872772 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[CH2:13]([O:15][CH2:16][CH2:17][N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[NH:27][C@@H:28]1[CH2:33][CH2:32][NH:31][C@@H:30]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:29]1)[CH3:14]>C(Cl)Cl>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([N:31]1[CH2:32][CH2:33][C@@H:28]([NH:27][C:19]2[N:18]([CH2:17][CH2:16][O:15][CH2:13][CH3:14])[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]=2)[CH2:29][C@@H:30]1[CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:4]

Participants

4

Reactant 2

HCID 8359Isatoic AnhydrideHCID 86755705HCID 86755705, compound

Product 1

HCID 86755704HCID 86755704, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isatoic anhydride (0.49 g) was added to a mixture of (±)-trans-1-(2-ethoxyethyl)-N-[2-(phenylmethyl)-4-piperidinyl]-1H-benzimidazol-2-amine (1.14 g) in CH2Cl2 (150 ml), the mixture was stirred for 3 hours and then refluxed for 3 hours. The solvent was evaporated, 2-propanol (100 ml) was added to the residue and the mixture was refluxed for 18 hours. Isatoic anhydride (0.2 g) was added again and the mixture was refluxed for 4 hours. The solvent was evaporated and the residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and evaporated. The residue was crystallized from DIPE, yielding 0.5 g (33.4%) of (±)-trans-1-[2-aminobenzoyl]-4-[[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]amino]-2-(phenylmethyl)piperidine (comp 123; mp. 197.4° C.).

Workup

  1. temperaturerefluxed for 3 hours
  2. customThe solvent was evaporated
  3. addition2-propanol (100 ml) was added to the residue
  4. temperaturethe mixture was refluxed for 18 hours
  5. additionIsatoic anhydride (0.2 g) was added again
  6. temperaturethe mixture was refluxed for 4 hours
  7. customThe solvent was evaporated
  8. customthe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5)
  9. customThe pure fractions were collected
  10. customevaporated
  11. customThe residue was crystallized from DIPE

Sources & evidence

ORD record
ord-a83e441195e642f49b74b02ea4820a3b
Source dataset
uspto-grants-2000_08
Patent number
US06110939

Reaction notes

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