Potassium Iodide → HCID 68829534, compound

HRID 747776Notes

Reaction equation

HRID 747776 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:23][CH2:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[C:29]#[N:30].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:23][CH2:24][O:25][C:26]3[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=3)[C:29]#[N:30])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 177889413-(2-bromoethoxy)benzonitrileHCID 22181157tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate

Product 1

HCID 68829534HCID 68829534, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

616 mg (1.91 mmol) of 1-t-butoxycarbonyl-4-(4-aminophenoxy)piperidine, 432 ml (1.91 mmol) of 3-(2-bromoethoxy)benzonitrile and 634 mg (3.82 mmol) of potassium iodide were dissolved in 20 ml of dimethylformamide. 2.64 g (19.1 mmol) of potassium carbonate was added to the solution, and they were stirred at room temperature for 14 hours. The solvent was distilled off under reduced pressure. After the treatment with ethyl acetate as extractant in an ordinary manner, the crude product was obtained. This product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customAfter the treatment with ethyl acetate as extractant in an ordinary manner, the crude product was obtained
  3. customThis product was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-21442828d21b4c33bd0871afa108cb0f
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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