Potassium Hydroxide → HCID 86755693, compound

HRID 1872766Notes

Reaction equation

HRID 1872766 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]2[CH2:15][C@H:14]([NH:16][C:17]3[N:21]([CH2:22][CH2:23][O:24][CH2:25][CH3:26])[C:20]4[CH:27]=[CH:28][CH:29]=[CH:30][C:19]=4[N:18]=3)[CH2:13][CH2:12][N:11]2C(OCC)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[K+]>CC(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]2[CH2:15][C@H:14]([NH:16][C:17]3[N:21]([CH2:22][CH2:23][O:24][CH2:25][CH3:26])[C:20]4[CH:27]=[CH:28][CH:29]=[CH:30][C:19]=4[N:18]=3)[CH2:13][CH2:12][NH:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86755689HCID 86755689, compound

Product 1

HCID 86755693HCID 86755693, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of (±)-ethyl trans-2-[(3,4-dichlorophenyl)methyl]-4-[[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate (2.5 g) and KOH (2.8 g) in 2-propanol (50 ml) was stirred and refluxed for 48 hours. The solvent was evaporated. The residue was partitioned between water and CH2Cl2. 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) 95/5, upgrading to 90/10). The pure fractions were collected and the solvent was evaporated, yielding 1.1 g (49.2%) of (±)-trans-N-[2-[(3,4-dichlorophenyl)methyl]-4-piperidinyl]-1-(2-ethoxyethyl)-1H-benzimidazol-2-amine (interm. 28).

Workup

  1. temperaturerefluxed for 48 hours
  2. customThe solvent was evaporated
  3. customThe residue was partitioned between water and CH2Cl2
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 95/5, upgrading to 90/10)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d90bda003d7a479083f2a4ca32f96d2b
Source dataset
uspto-grants-2000_08
Patent number
US06110939

Reaction notes

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