Sodium Hydroxide → HCID 66836000, compound

HRID 572852Notes

Reaction equation

HRID 572852 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](Cl)Cl.[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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 66835904HCID 66835904, compound

Product 1

HCID 66836000HCID 66836000, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[(1-methylpiperidin-4-yloxy)(3-nitrophenyl)methyl]-1H-benzimidazole (110 mg) in ethanol is added tin(II)dichloride (340 mg). The reaction mixture is refluxed for 2 hours. The solution is basified by adding a solution of 10N sodium hydroxide to pH 10. The aqueous phase is extracted with chloroform. The pooled organic extracts are dried over magnesium sulfate 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 melting at 100° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours
  2. extractionThe aqueous phase is extracted with chloroform
  3. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 98/2/0.2 to 90/10/1)

Sources & evidence

ORD record
ord-33923122c2754a7cad30d83dcc63731b
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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