Sodium Iodide → 1-(4-Nitrobenzyl)piperidine

HRID 1007119Notes

Reaction equation

HRID 1007119 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].CC1(C)CC1C(N[CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)=O>CN(C)C=O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:30]2[CH2:31][CH2:32][CH2:27][CH2:28][CH2:29]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 22667753HCID 22667753, compound

Product 1

HCID 7835411-(4-Nitrobenzyl)piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-nitrobenzyl bromide (24:X=Br) (110 mg, 0.5 mmol), potassium carbonate (352 mg, 2.55 mmol) and sodium iodide (76.5 mg, 0.5 mmol) were added to a dimethylformamide (5mil) solution of the piperidine (23) obtained in the process 1, and then stirred under the argon atmosphere at the room temperature for 2 hours. This was further stirred at 70° C. for 1 hour and was extracted with hexan-ethyl acetate (3:1) mixed solvent, and then washed with water and saturated saline solution, dried and vacuum concentrated, thus obtained a 4-nitrobenzylpiperadine compound (25:R=2,2-dimethylcyclopropane) in the form of a yellow crystal (95 mg, 57%).

Workup

  1. customobtained in the process 1
  2. stirringThis was further stirred at 70° C. for 1 hour
  3. extractionwas extracted with hexan-ethyl acetate (3:1)
  4. additionmixed solvent
  5. washwashed with water and saturated saline solution
  6. customdried
  7. concentrationvacuum concentrated

Sources & evidence

ORD record
ord-82a7babff15d466b9a01ec6352c3850b
Source dataset
uspto-grants-2004_09
Patent number
US06794378B2

Reaction notes

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