Acetic Acid → HCID 20343971, compound

HRID 2049885Notes

Reaction equation

HRID 2049885 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2([C:23]#[N:24])[CH2:20][CH2:19][N:18](C#N)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1.C(O)(=O)C>O.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2([C:23]#[N:24])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 20343954HCID 20343954, compound

Product 1

HCID 20343971HCID 20343971, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1.2 g of 4-[2-(4-chlorophenylthio)phenyl]-1,4-dicyanopiperidine, Example 24, and 15 ml of a glacial acetic acid 3 N hydrochloric acid (1:2) solution is stirred at 110° C. for 24 hours. Thereafter, the solution is diluted with 80 ml of water before being evaporated to dryness. The solid residue is made strongly basic with ammonium hydroxide and the alkaline solution is extracted with ether. The combined ether extracts are successively dried, filtered and concentrated to dryness, leaving a white solid. The solid is dissolved in methylene chloride and this solution is chromatographed (silica gel/methylene chloride column, 10% methyl alcohol in methylene chloride as eluant). The desired fractions are concentrated to dryness. The resulting material is recrystallized from cyclohexane to provide 4-[2-(4-chlorophenylthio)phenyl]-4-cyanopiperidine.

Workup

  1. custombefore being evaporated to dryness
  2. extractionthe alkaline solution is extracted with ether
  3. dry with materialThe combined ether extracts are successively dried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customleaving a white solid
  7. customthis solution is chromatographed (silica gel/methylene chloride column, 10% methyl alcohol in methylene chloride as eluant)
  8. concentrationThe desired fractions are concentrated to dryness
  9. customThe resulting material is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-92973a21a12c488d94039f0ff68df6dc
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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