Sodium Hydroxide → 2-((1-Benzylpiperidin-4-yl)oxy)ethanol

HRID 329026Notes

Reaction equation

HRID 329026 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:11]([N:18]1[CH2:27][CH2:26][C:21]2([O:25][CH2:24][CH2:23][O:22]2)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>CCOCC.O>[CH2:11]([N:18]1[CH2:19][CH2:20][CH:21]([O:22][CH2:23][CH2:24][OH:25])[CH2:26][CH2:27]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 7264498-Benzyl-1,4-dioxa-8-azaspiro[4.5]decaneHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 202953472-((1-Benzylpiperidin-4-yl)oxy)ethanolYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

106.8 g of (0.8 mole) of aluminum chloride were added to a 2 liter, 3-neck flask and then 800 ml of anhydrous ether were added thereto with strong cooling. The mixture was stirred for 30 minutes and then a suspension of 7.6 g (0.2 mole) of lithium aluminum hydride in 200 ml of ether was added thereto. The mixture was stirred for 30 minutes and then a solution of 93.2 g (0.4 mole) of 8-benzyl-1,4-dioxa-8-aza-spiro [4,5] decane in 400 ml of anhydrous ether was added thereto dropwise. After the addition, stirring was continued at room temperature for 2 hours and 1 liter of water was then slowly added with strong cooling. The mixture was made alkaline with 90 g of sodium hydroxide pellets and the ether phase was decanted off. The aqueous layer was extracted again with ether and the combined ether phases were dried and the ether removed by distillation. The residue was distilled to obtain 63 g (67% yield) of 2-[1-benzyl-4-piperidyloxy]-ethanol in the form of a clear oil boiling at 140° C at 0.1 mm Hg and having a refractive index nD20 = 1.633.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 30 minutes
  3. additionAfter the addition
  4. stirringstirring
  5. waitwas continued at room temperature for 2 hours
  6. customthe ether phase was decanted off
  7. extractionThe aqueous layer was extracted again with ether
  8. dry with materialthe combined ether phases were dried
  9. customthe ether removed by distillation
  10. distillationThe residue was distilled

Sources & evidence

ORD record
ord-eff47d7de94a413385251666cee7d8b0
Source dataset
uspto-grants-1977_04
Patent number
US04018922

Reaction notes

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