Hydrochloric Acid → HCID 20343972, compound

HRID 2049882Notes

Reaction equation

HRID 2049882 reaction equation
C([N:3]1[CH2:8][CH2:7][C:6]([C:23]#[N:24])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:5][CH2:4]1)#N.Cl>C(O)(=O)C.O>[C:23]([C:6]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15][C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]1)#[N:24]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 20344019HCID 20344019, compound

Product 1

HCID 20343972HCID 20343972, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2.0 g of 1,4-dicyano-4-[2-(4-fluorophenylthio)phenyl]piperidine, Example 29, in 12 ml of glacial acetic acid and 21 ml of 3 N hydrochloric acid is stirred at 110°-120° C. for 18 hours. Thereafter, the solution is diluted with 50 ml of water and the diluted solution is rotary evaporated twice to near dryness. The residual material is diluted in 100 ml of water and 2 ml of 58% ammonium hydroxide, giving a milky solution at pH 9. This aqueous suspension is extracted thrice with 150 ml portions of a benzene-ether (1:1) mixture. The combined extracts are washed, first with 50 ml of water and then with 25 ml saturated sodium chloride solution, and dried. The residual material is recrystallized from a benzene-hexane mixture to provide 4-cyano-4-[2-(4-fluorophenylthio)phenyl]piperidine.

Workup

  1. customthe diluted solution is rotary evaporated twice
  2. additionThe residual material is diluted in 100 ml of water
  3. custom2 ml of 58% ammonium hydroxide, giving a milky solution at pH 9
  4. extractionThis aqueous suspension is extracted thrice with 150 ml portions of a benzene-ether (1:1) mixture
  5. washThe combined extracts are washed, first with 50 ml of water
  6. dry with materialwith 25 ml saturated sodium chloride solution, and dried
  7. customThe residual material is recrystallized from a benzene-hexane mixture

Sources & evidence

ORD record
ord-d66ef75139e34361bd19d3fca7bf58d0
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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