Diethyl Ether → 4-[3-[(Trifluoromethyl)thio]phenyl]-1-piperazinepropanenitrile

HRID 437345Notes

Reaction equation

HRID 437345 reaction equation
[F:1][C:2]([F:17])([F:16])[S:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[C:18](#[N:21])[CH:19]=[CH2:20].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.C(OCC)C>CO>[C:18]([CH2:19][CH2:20][N:13]1[CH2:12][CH2:11][N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([S:3][C:2]([F:1])([F:16])[F:17])[CH:5]=2)[CH2:15][CH2:14]1)#[N:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 30165571-(3-((Trifluoromethyl)thio)phenyl)piperazine

Product 1

HCID 214283314-[3-[(Trifluoromethyl)thio]phenyl]-1-piperazinepropanenitrileYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(m-trifluoromethylthiophenyl)-piperazine (10.8 g, 0.047 g.mol.) and acrylonitrile (4.9 g, 0.094 g. mol.) are introduced into a 50 ml round bottomed flask provided with a stirrer and a reflux condenser. 0.1 ml of a 40% solution of benzyltrimethylammonium hydroxide in methyl alcohol is added with cooling and stirring. The mixture is allowed to stand at ambient temperature for 2 days and then heated for 2 hours to 80° C. After cooling, anhydrous diethyl ether (100 ml) is added to the reaction mixture, insoluble materials are filtered off, and the solution obtained evaporated on a water-bath in vacuo. The residue is fractionally distilled and N-(β-cyano-ethyl)-N'-(m-trifluoromethylthiophenyl)-piperazine (11 g, 88% yield) is thus obtained as a clear yellow viscous liquid, b.p. 198°-200°/3 mm Hg, nD23 = 1.5378.

Workup

  1. customprovided with a stirrer and a reflux condenser
  2. temperaturewith cooling
  3. temperatureheated for 2 hours to 80° C
  4. temperatureAfter cooling
  5. filtrationare filtered off
  6. customthe solution obtained
  7. customevaporated on a water-bath in vacuo
  8. distillationThe residue is fractionally distilled

Sources & evidence

ORD record
ord-41b1d57e7b2d4b39a84558c9905c32fe
Source dataset
uspto-grants-1977_06
Patent number
US04031094

Reaction notes

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