Hydrochloric Acid → HCID 20283067, compound

HRID 463321Notes

Reaction equation

HRID 463321 reaction equation
[ClH:1].Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:15][CH2:16][CH2:17][N:18]([CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[F:35])[CH2:24][CH2:23]3)[CH3:19])OCC[O:11]2)=[CH:6][CH:5]=1.Cl.C(=O)(O)[O-].[Na+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>CO>[ClH:1].[ClH:1].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:11])[CH2:15][CH2:16][CH2:17][N:18]([CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH:25]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[F:35])[CH2:26][CH2:27]2)[CH3:19])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 516892Sodium BicarbonateHCID 20283059HCID 20283059, compound

Product 1

HCID 20283067HCID 20283067, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 17.8 g (33.4 mol) of 1-{2-{N-{3-[(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylamino}ethyl}-4-(2-fluorophenoxy)piperidine dihydrochloride, 260 ml methanol and 110 ml 3N HCl was heated at reflux for 3 hours under nitrogen and cooled to room temperature. The solution was neutralized with saturated sodium bicarbonate and the methanol evaporated. The residue was made basic with sodium carbonate, extracted twice with ether, washed with saturated sodium chloride and dried over potassium carbonate. Evaporation of the solvent provided an oil. The yield of the dihydrochloride was 14.9 g (30.4 mmol). Recrystallization from ethanol provided 12.25 g (75%) of the desired ketone.

Workup

  1. temperatureat reflux for 3 hours under nitrogen
  2. customthe methanol evaporated
  3. extractionextracted twice with ether
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over potassium carbonate
  6. customEvaporation of the solvent
  7. customprovided an oil
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-65ab803c8cd74f608215a43a502381f0
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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