Water → HCID 66836000, compound

HRID 2404442Notes

Reaction equation

HRID 2404442 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=2)[C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]=2)[CH2:4][CH2:3]1.[Sn+2].O.O.[Cl-].[Cl-].O.[OH-].[Na+]>C(O)C>[NH:11]1[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=[C:10]1[CH:9]([O:8][CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1)[C:19]1[CH:20]=[C:21]([NH2:25])[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 1019843610025-69-1HCID 66835904HCID 66835904, compound

Product 1

HCID 66836000HCID 66836000, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[(1-Methyl-piperidin-4-yloxy)-(3-nitro-phenyl)-methyl]-1H benzimidazole (110 mg) in ethanol (5 mL) is added Tin(II)dichloride-dihydrate (340 mg). The reaction mixture is heated at reflux for 2 hours. Water is added to the mixture as well as sodium hydroxide 1N solution to pH 10 The solution is extracted with chloroform. The pooled organic phases are dried with magnesium sulphate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 98/2/0.2 to 90/10/1) to give 3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]phenylamine that is used without further purification.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2 hours
  3. extractionis extracted with chloroform
  4. dry with materialThe pooled organic phases are dried with magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 98/2/0.2 to 90/10/1)

Sources & evidence

ORD record
ord-17ff6f04536a41a5983946b6c430783b
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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