Sodium sulfate decahydrate → HCID 22181195, compound

HRID 1796198Notes

Reaction equation

HRID 1796198 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:10]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=2[Cl:24])[CH2:12][CH2:11]1)(=O)[CH3:8].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Cl:24][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:17]=1[O:16][CH:13]1[CH2:14][CH2:15][N:10]([CH2:7][CH3:8])[CH2:11][CH2:12]1)[NH2:21]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydride2×HCID 22181010HCID 22181010, compound

Product 1

HCID 22181195HCID 22181195, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (230 mg) in tetrahydrofuran (5 ml) was added dropwise a solution of 4-(1-acetylpiperidin-4-yloxy)-3-chloroaniline obtained in reference example 10 in tetrahydrofuran (10 ml) with stirring under ice-cooling in a nitrogen atmosphere, and the resulting mixture was refluxed for 3.5 hours. After refluxing, to the reaction mixture was furthermore added lithium aluminum hydride (115 mg), and the resulting mixture was refluxed for a further 2 hours. After cooling to room temperature, to the reaction mixture was added sodium sulfate decahydrate, and the resulting mixture was furthermore stirred at room temperature overnight. After removing insoluble materials by filtration, the filtrate was evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of dichloromethane and methanol (3:1˜1:2) as the eluent to afford the title compound (448 mg, yield: 58%) as a brown oil.

Workup

  1. temperaturecooling in a nitrogen atmosphere
  2. temperaturethe resulting mixture was refluxed for 3.5 hours
  3. temperatureAfter refluxing, to the reaction mixture
  4. temperaturethe resulting mixture was refluxed for a further 2 hours
  5. stirringthe resulting mixture was furthermore stirred at room temperature overnight
  6. customAfter removing insoluble materials
  7. filtrationby filtration
  8. customthe filtrate was evaporated in vacuo
  9. customThe residue obtained
  10. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-0c6eaa4cd12b4169895b01562066de18
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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