Hydrochloric Acid → HCID 21428333, compound

HRID 437346Notes

Reaction equation

HRID 437346 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]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[ClH:36]>CO.O.C(O)(C)C>[ClH:36].[CH3:23][O:22][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)=[O:21]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 30165571-(3-((Trifluoromethyl)thio)phenyl)piperazine

Product 1

HCID 21428333HCID 21428333, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

N-(m-trifluoromethylthiophenyl)-piperazine (7 g, 0.0267 g.mol) and freshly distilled methyl acrylate (2.55 g, 0.0295 g.mol.) are introduced in a 50 ml round bottomed flask provided with a stirrer and reflux condenser. The temperature rises slightly. The mixture is allowed to cool and 0.1 ml of a 40% solution of benzyltrimethylammonium hydroxide in methyl alcohol is then added with stirring. The mixture is allowed to stand for 2 days at ambient temperature. Boiling isopropyl alcohol (60 ml) is then added and the mixture is acidified by addition of concentrated hydrochloric acid (2.3 ml). The solvents are removed on a water-bath in vacuo and the residue is treated twice with benzene (50 ml each time) which is distilled off to remove water azeotropically. The residue is then taken up in isopropyl alcohol (50 ml) and the solution is filtered hot and allowed to stand several hours in a refrigerator. The precipitate formed is separated and dried in vacuo over phosphorous pentoxide. N-(β-methoxycarbonyl-ethyl)-N'-(m-trifluoromethylthiophenyl)-piperazine hydrochloride (8.2 g, 80% yield) is thus obtained as a white crystalline powder, m.p. 180° C, soluble in water.

Workup

  1. customprovided with a stirrer
  2. temperaturereflux condenser
  3. temperatureto cool
  4. customThe solvents are removed on a water-bath in vacuo
  5. additionthe residue is treated twice with benzene (50 ml each time) which
  6. distillationis distilled off
  7. customto remove water azeotropically
  8. filtrationthe solution is filtered hot
  9. waitto stand several hours in a refrigerator
  10. customThe precipitate formed
  11. customis separated
  12. dry with materialdried in vacuo over phosphorous pentoxide

Sources & evidence

ORD record
ord-3921dba3e7fe462f9475b5c24a401a0b
Source dataset
uspto-grants-1977_06
Patent number
US04031094

Reaction notes

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