Hydrochloric Acid → HCID 23044992, compound

HRID 2107950Notes

Reaction equation

HRID 2107950 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[ClH:32]>C1(C)C=CC=CC=1.CCOCC.CCO>[ClH:1].[ClH:32].[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:4][CH2:3][CH2:2][N:29]2[CH2:30][CH2:31][N:26]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=3)[CH2:27][CH2:28]2)=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 944591-(2-Pyridyl)piperazine

Product 1

HCID 23044992HCID 23044992, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

3.3 g (0.01 mole) of 1-chloro-4,4-bis(p-fluorophenyl)butane, 3.3 g (0.02 mole) of 1-(2-pyridyl)-piperazine and 0.05 g of KI were refluxed in 15 ml of toluene for 48 h. After cooling and addition of ether (30 ml) 1-(2-pyridyl)-piperazine hydrochloride precipitated and was filtered off. After subsequent washing several times with H2O the organic layer was dried with K2CO3. Evaporation of the solvent yielded the crude base. This was dissolved in ether and HCl in EtOH was added to precipitate the hydrochloride. Recrystallization from EtOAc/EtOH yielded 3.2 g (67%) of the title compound (2:1), m.p. 224°-27° C.

Workup

  1. temperatureAfter cooling
  2. customprecipitated
  3. filtrationwas filtered off
  4. dry with materialAfter subsequent washing several times with H2O the organic layer was dried with K2CO3
  5. customEvaporation of the solvent
  6. customyielded the crude base
  7. customto precipitate the hydrochloride
  8. customRecrystallization from EtOAc/EtOH

Sources & evidence

ORD record
ord-a0e16689997b4808b4dc42bd6f95e123
Source dataset
uspto-grants-1990_06
Patent number
US04937245

Reaction notes

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