3,4-Difluoroaniline → HCID 21852751, compound

HRID 1586382Notes

Reaction equation

HRID 1586382 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[ClH:10].Br[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]Br>ClC1C=CC=CC=1.C(OCC)C>[ClH:10].[ClH:10].[F:1][C:2]1[CH:3]=[C:4]([N:5]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[F:9]

Participants

5

Reactant 2

HCID 774693,4-DifluoroanilineHCID 21852743HCID 21852743, compound

Product 1

HCID 21852751HCID 21852751, compoundYield 201.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 3,4-difluoroaniline (3.6 g) and bis(2-bromoethyl)amine hydrochloride (5.0 g) in 50 mL of chlorobenzene is warmed to reflux under argon for 48 hours. The mixture is cooled to room temperature, diluted with 100 mL of diethyl ether, and extracted with three 150 mL portions of 1N HCl. The aqueous extracts are backwashed with three 50 mL portions of ether, which are discarded. The combined aqueous fractions are basified to pH 11 with 12N NaOH. The resulting mixture is extracted with three 50 mL portions of methylene chloride, and the combined organic extracts are dried over sodium sulfate. The solvent is removed under reduced pressure, and the resulting residue is taken up in 50 mL of diethyl ether and filtered through Celite. The resulting solution is treated with a 1 M ethereal HCl solution (56 mL), and the resulting precipitate is collected and dried under vacuum to give 5.1 g of the title compound, mp 100-104° C. (decomposes). ##STR7## Preparation of 2-[4-(3,4-difluoro-phenyl)-piperazin-1-ylmethyl]-quinoline

Workup

  1. temperatureis warmed
  2. temperatureto reflux under argon for 48 hours
  3. extractionextracted with three 150 mL portions of 1N HCl
  4. extractionThe resulting mixture is extracted with three 50 mL portions of methylene chloride
  5. dry with materialthe combined organic extracts are dried over sodium sulfate
  6. customThe solvent is removed under reduced pressure
  7. filtrationfiltered through Celite
  8. additionThe resulting solution is treated with a 1 M ethereal HCl solution (56 mL)
  9. customthe resulting precipitate is collected
  10. customdried under vacuum

Sources & evidence

ORD record
ord-07059e2037874e019dcc6218fc10cb63
Source dataset
uspto-grants-1999_08
Patent number
US05945421

Reaction notes

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