Sodium sulfate decahydrate → HCID 19370376, compound

HRID 129754Notes

Reaction equation

HRID 129754 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:15]1([C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:11]2[CH2:10][CH2:9][N:8]([CH2:7][CH2:6][CH2:5][NH:4][CH2:1][CH3:2])[CH2:13][CH2:12]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 19370268HCID 19370268, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 19370376HCID 19370376, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.14 g of 1-(3-acetamidopropyl)-4-(diphenylmethylene)piperidine (prepared as described in Preparation 33') in 7 ml of tetrahydrofuran was added dropwise to a suspension of 140 mg of lithium aluminum hydride in 10 ml of tetrahydrofuran at room temperature under a nitrogen atmosphere, and the mixture was heated under reflux for 4 hours. At the end of this time, the mixture was cooled to room temperature, and sodium sulfate decahydrate was added to the mixture to decompose excess lithium aluminum hydride. The insoluble material was removed by filtration. Ethyl acetate was added to the filtrate, and the mixture was washed with water and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. Evaporation of solvent under reduced pressure gave 710 mg (yield 65%) of the title compound as an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customThe insoluble material was removed by filtration
  4. additionEthyl acetate was added to the filtrate
  5. washthe mixture was washed with water and with a saturated aqueous solution of sodium chloride, in that order
  6. dry with materialafter which it was dried over anhydrous magnesium sulfate
  7. customEvaporation of solvent under reduced pressure

Sources & evidence

ORD record
ord-fd9fe864615441e8a859a660bad4de9e
Source dataset
uspto-grants-1995_11
Patent number
US05470851

Reaction notes

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