Sodium Iodide → 1-Cyanomethyl-4-(4-phenoxyphenyl)piperidine

HRID 966

Reaction equation

HRID 966 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:21][C:22]#[N:23].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:22]([CH2:21][N:17]1[CH2:18][CH2:19][CH:14]([C:11]2[CH:12]=[CH:13][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:9][CH:10]=2)[CH2:15][CH2:16]1)#[N:23]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 110759844-(4-Phenoxyphenyl)piperidine

Product 1

HCID 196942431-Cyanomethyl-4-(4-phenoxyphenyl)piperidineYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an 8 ml dimethylformamide solution of 300 mg of the compound (4) synthesized in Reference Example 4 were added 93 mg of chloroacetonitrile, 355 mg of sodium iodide, and 196 mg of potassium carbonate. This was then heated at reflux for 2 hours. To the reaction was added 10 ml of ice water, then extraction was performed with ethyl acetate. The extract was dried, filtered, then concentrated under reduced pressure to obtain a residue which was then purified by silica gel column chromatography (methylene chloride:methanol =30:1) to obtain the above-identified compound (26) in an amount of 313 mg (yield of 91%).

Workup

  1. temperatureThis was then heated
  2. temperatureat reflux for 2 hours
  3. extractionextraction
  4. customThe extract was dried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a residue which
  8. customwas then purified by silica gel column chromatography (methylene chloride:methanol =30:1)

Sources & evidence

ORD record
ord-29bdac8cd38e44e3a6167a6148c0ca92
Source dataset
uspto-grants-1998_03
Patent number
US05723475

Linked notes

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