Sodium Hydroxide → HCID 21699585, compound

HRID 1597265Notes

Reaction equation

HRID 1597265 reaction equation
[C:1]([NH:4][C:5]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1.O>[CH2:11]([N:8]1[CH2:7][CH2:6][C:5]([NH:4][CH2:1][CH3:2])([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:10][CH2:9]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 18964199N-(1-Benzyl-4-phenylpiperidin-4-YL)acetamideHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 21699585HCID 21699585, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent4×

Procedure

A solution of 5 g of 4-acetamido-1-benzyl-4-phenylpiperidine in 50 ml of THF is added to a suspension of 1.5 g of lithium aluminum hydride in 20 ml of THF and the mixture is refluxed for 3 hours. After cooling, a solution of 1 ml of concentrated NaOH in 8 ml of water is added, the inorganic salts are filtered and the filtrate is evaporated under vacuum. The oil obtained is dissolved in 50 ml of THF, this solution is added to a suspension of 1.5 ml of lithium aluminum hydride in 20 ml of THF and the mixture is refluxed for 1 hour. The reaction mixture is hydrolyzed by addition of a solution of 0.5 ml of concentrated NaOH in 6 ml of water, the inorganic salts filtered and the filtrate evaporated under vacuum. 4.8 g of the expected product are obtained, which product is used as it is in the next stage.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. temperatureAfter cooling
  3. filtrationthe inorganic salts are filtered
  4. customthe filtrate is evaporated under vacuum
  5. customThe oil obtained
  6. temperaturethe mixture is refluxed for 1 hour
  7. filtrationthe inorganic salts filtered
  8. customthe filtrate evaporated under vacuum

Sources & evidence

ORD record
ord-06eac4be04eb461d9562308dfd91ae33
Source dataset
uspto-grants-2001_09
Patent number
US06294537B1

Reaction notes

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