Sodium Carbonate → HCID 20283059, compound

HRID 463320Notes

Reaction equation

HRID 463320 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([CH2:19][CH2:20][CH2:21][N:22]([CH2:24][C:25]([N:27]3[CH2:32][CH2:31][CH:30]([O:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[F:40])[CH2:29][CH2:28]3)=O)[CH3:23])[O:18][CH2:17][CH2:16][O:15]2)=[CH:10][CH:9]=1.C([O-])(=O)C([O-])=O.[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:67].Cl>C1COCC1.O>[ClH:67].[ClH:67].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([CH2:19][CH2:20][CH2:21][N:22]([CH2:24][CH2:25][N:27]3[CH2:28][CH2:29][CH:30]([O:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[F:40])[CH2:31][CH2:32]3)[CH3:23])[O:15][CH2:16][CH2:17][O:18]2)=[CH:10][CH:9]=1

Participants

9

Reactant 6

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 71081OxalateHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 20283076HCID 20283076, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20283059HCID 20283059, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 7.38 g (0.503 mol) of lithium aluminum hydride (50% in oil; washed 3 times with hexanes) in 250 ml of dry THF at 0° was added dropwise a solution of 1-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-(2-fluorophenoxy)piperidine (liberated from 28.6 g, 50.6 mmol, of the oxalate) in 250 ml of THF. The mixture was allowed to warm to room temperature and subsequently heated at reflux for 24 hours under nitrogen. The mixture was allowed to cool to room temperature and subsequently cooled in an ice bath. To the mixture were added dropwise, slowly, 4 ml water, 4 ml 15% sodium hydroxide and 12 ml water. The suspension was filtered and the residue washed with THF. Evaporation of the solvent provided an oil which was shaken with saturated sodium carbonate, extracted twice with ether, washed with saturated sodium chloride and dried over potassium carbonate. Filtration followed by evaporation of the solvent provided an oil. The yield of the dihydrochloride was 20.26 g (44.0 mmol, 87%).

Workup

  1. temperaturesubsequently heated
  2. temperatureat reflux for 24 hours under nitrogen
  3. temperatureto cool to room temperature
  4. temperaturesubsequently cooled in an ice bath
  5. additionTo the mixture were added dropwise
  6. filtrationThe suspension was filtered
  7. washthe residue washed with THF
  8. customEvaporation of the solvent
  9. customprovided an oil which
  10. extractionextracted twice with ether
  11. washwashed with saturated sodium chloride
  12. dry with materialdried over potassium carbonate
  13. filtrationFiltration
  14. customfollowed by evaporation of the solvent
  15. customprovided an oil

Sources & evidence

ORD record
ord-1cb89353033449a397cd1675a234f926
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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