Sodium Hydroxide → HCID 20283107, compound

HRID 463322Notes

Reaction equation

HRID 463322 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]([Cl: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.O>[ClH:40].[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]([Cl: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

8

Reactant 5

HCID 14798Sodium HydroxideHCID 71081OxalateHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 202831261-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-propyl}-N-methylaminoacetyl}-4-(4-chlorophenoxy)piperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 20283107HCID 20283107, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 4.68 g of lithium aluminum hydride (61.7 mmol, 50% in oil; washed 3 times with hexane) in 160 ml of THF was added dropwise a solution of 1-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-propyl}-N-methylaminoacetyl}-4-(4-chlorophenoxy)piperidine (liberated from 34.7 g, 0.105 mol, of the oxalate) in 160 ml of dry THF. The mixture was stirred at reflux for 16 hours, allowed to cool to room temperature and subsequently cooled in an ice bath. To the mixture were added slowly, dropwise, 3 ml of water, 3 ml of 15% NaOH and 9 of ml water. The mixture was filtered and the residue washed with THF. Evaporation of the solvent provided an oil. The oil was washed with water, dried over potassium carbonate and the solvent evaporated to provide an oil. The yield of the dihydrochloride was 11.98 g (63%).

Workup

  1. temperatureat reflux for 16 hours
  2. temperaturesubsequently cooled in an ice bath
  3. additionTo the mixture were added slowly
  4. filtrationThe mixture was filtered
  5. washthe residue washed with THF
  6. customEvaporation of the solvent
  7. customprovided an oil
  8. washThe oil was washed with water
  9. dry with materialdried over potassium carbonate
  10. customthe solvent evaporated
  11. customto provide an oil

Sources & evidence

ORD record
ord-6fa1964ba6764794a09448a348080666
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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