Sodium Hydroxide → HCID 20283055, compound

HRID 463318Notes

Reaction equation

HRID 463318 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][C:37]([F:40])=[CH:36][CH:35]=4)[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+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:61].Cl>C1COCC1.CCOCC.O>[ClH:61].[ClH:61].[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:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=4)[CH2:31][CH2:32]3)[CH3:23])[O:15][CH2:16][CH2:17][O:18]2)=[CH:10][CH:9]=1

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 71081OxalateHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 20283102HCID 20283102, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20283055HCID 20283055, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1.4 g (21.1 mmol) of lithium aluminum hydride (57% in oil; washed 3 times with hexane) in 50 ml of dry THF, cooled at 0°, was added dropwise a solution of 1-{N-{3-[2-(4-Fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-(4-fluorophenoxy)piperidine (liberated from 5.94 g (10.5 mmol) of the oxalate) in 50 ml of dry THF. The mixture was allowed to warm to room temperature and was then heated at reflux for 16 hours under nitrogen, allowed to cool to room temperature and subsequently cooled in an ice bath. To the mixture were added dropwise, slowly, 0.7 ml of water, 0.7 ml of 15% NaOH and 2 ml of water. The mixture was filtered and washed with 100 ml of THF. The solvent was evaporated from the filtrate to provide an oil. The oil was dissolved in ether, washed with water and saturated sodium chloride and dried over potassium carbonate. Filtration followed by evaporation of the solvent provided an oil. The yield of the dihydrochloride was 3.83 g (68%). Recrystallization from ethanol provided analytically pure material.

Workup

  1. temperaturecooled at 0°
  2. temperaturewas then heated
  3. temperatureat reflux for 16 hours under nitrogen
  4. temperatureto cool to room temperature
  5. temperaturesubsequently cooled in an ice bath
  6. additionTo the mixture were added dropwise
  7. filtrationThe mixture was filtered
  8. washwashed with 100 ml of THF
  9. customThe solvent was evaporated from the filtrate
  10. customto provide an oil
  11. washwashed with water and saturated sodium chloride
  12. dry with materialdried over potassium carbonate
  13. filtrationFiltration
  14. customfollowed by evaporation of the solvent
  15. customprovided an oil
  16. customRecrystallization from ethanol
  17. customprovided analytically pure material

Sources & evidence

ORD record
ord-b461fbf8231046f5b5a51b47ceb91ade
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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