Acetic Acid → HCID 20343823, compound

HRID 2049893Notes

Reaction equation

HRID 2049893 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2([C:21]#[N:22])[CH2:18][CH2:17][N:16](C#N)[CH2:15][CH2:14]2)=[CH:4][CH:3]=1.C(O)(=O)C>O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2([C:21]#[N:22])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 20343872HCID 20343872, compound

Product 1

HCID 20343823HCID 20343823, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1.2 g of 4-[2-(4-chlorophenoxy)phenyl]-1,4-dicyanopiperidine, Example 23, 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 leaving an oil which solidifies on standing to a white granular material, mp 128°-130° C. This material, for purposes of obtaining an analytical sample, is recrystallized from cyclohexane to provide white needles of 4-[2-(4-chlorophenoxy)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. customleaving an oil which
  10. customThis material, for purposes of obtaining an analytical sample
  11. customis recrystallized from cyclohexane

Sources & evidence

ORD record
ord-f171882bbb8f460da34ea286215016cf
Source dataset
uspto-grants-1980_04
Patent number
US04198417

Reaction notes

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