Hydrochloric Acid → HCID 20283071, compound

HRID 463319Notes

Reaction equation

HRID 463319 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](OC4C=CC(F)=CC=4)[CH2:24][CH2:23]3)[CH3:19])[O:14]CCO2)=[CH:6][CH:5]=1.Cl.[C:37]1(N)[C:42]([F:43])=[C:41](F)[C:40](F)=[C:39](N)[C:38]=1F.Cl.Cl>CO>[ClH:1].[ClH:1].[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:14])[CH2:15][CH2:16][CH2:17][N:18]([CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH:25]([C:39]3[CH:38]=[CH:37][C:42]([F:43])=[CH:41][CH:40]=3)[CH2:26][CH2:27]2)[CH3:19])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 20283055HCID 20283055, compound

Product 1

HCID 20283071HCID 20283071, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 11.4 g (21.4 mmol) of 1-{2-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylamino}ethyl}-4-(4-fluorophenoxy)piperidine dihydrochloride, 260 ml of methanol and 130 ml of 3N HCl was heated at reflux for 3 hours under nitrogen. The mixture was allowed to cool to room temperature and the methanol evaporated. The mixture was made basic with saturated 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 8.38 g (79.9%). Recrystallization from ethanol/methanol provided analytically pure material.

Workup

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

Sources & evidence

ORD record
ord-8b13c3ba2a754b34bb27735ddde71a91
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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