Potassium Iodide → alpha-(4-Methylphenyl)-1-(phenylmethyl)-4-piperidineacetonitrile monohydrochloride

HRID 66671Notes

Reaction equation

HRID 66671 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:9]#[N:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[Cl:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O.CC(C)CC(=O)C>[ClH:25].[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:11]2[CH2:12][CH2:13][N:14]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:15][CH2:16]2)[C:9]#[N:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 10340Sodium CarbonateHCID 20530716alpha-(4-Methylphenyl)-4-piperidineacetonitrile

Product 1

HCID 13035938alpha-(4-Methylphenyl)-1-(phenylmethyl)-4-piperidineacetonitrile monohydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a mixture of 74 parts of dl-α-(4-methylphenyl)-4-piperidineacetonitrile, 95.4 parts of sodium carbonate, a few crystals of potassium iodide in 1840 parts of 4-methyl-2-pentanone are added portionwise 39.21 parts of (chloromethyl)benzene. After the addition is complete, the whole is stirred and refluxed for 24 hours. The reaction mixture is cooled and 400 parts of water are added. The organic layer is separated, dried over potassium carbonate, filtered and evaporated. The oily residue is dissolved in 1,1'-oxybisethane and gazeous hydrogen chloride is introduced into the solution. The precipitated hydrochloride salt is filtered off and dried, yielding 68 parts of dl-α-(4-methylphenyl)-1-(phenylmethyl)-4-piperidineacetonitrile monohydrochloride; mp. 212°-213° C.

Workup

  1. additionAfter the addition
  2. temperaturerefluxed for 24 hours
  3. temperatureThe reaction mixture is cooled
  4. customThe organic layer is separated
  5. dry with materialdried over potassium carbonate
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe oily residue is dissolved in 1,1'-oxybisethane
  9. additiongazeous hydrogen chloride is introduced into the solution
  10. filtrationThe precipitated hydrochloride salt is filtered off
  11. customdried

Sources & evidence

ORD record
ord-9704f32e50604b2286dd4b5de00f0a6f
Source dataset
uspto-grants-1982_08
Patent number
US04342870

Reaction notes

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