Hydroxide → 1-(2-Anilinoethyl)-4-methoxymethoxypiperidine

HRID 2257894Notes

Reaction equation

HRID 2257894 reaction equation
[NH:1]([C:8]([CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][O:19][CH3:20])[CH2:13][CH2:12]1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].O>O1CCCC1.C(OCC)(=O)C>[NH:1]([CH2:8][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][O:19][CH3:20])[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 961HydroxideHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 229236881-(Anilinocarbonylmethyl)-4-methoxymethoxypiperidine

Product 1

HCID 229237061-(2-Anilinoethyl)-4-methoxymethoxypiperidineYield 98.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3.64 g of 1-(anilinocarbonylmethyl)-4-methoxymethoxypiperidine in 10 ml of tetrahydrofuran was added to a suspension of 630 mg of lithium aluminum hydride in 50 ml of tetrahydrofuran. The mixture was refluxed for 3 hours. To the reaction mixture were added 1.5 ml of an aqueous solution containing 10% of potassim hydroxide and 1.5 ml of water. The mixture was diluted with ethyl acetate, and the dilution was filtered. The solvent in the filtrate was removed by distillation to obtain 3.41 g of 1-(2-anilinoethyl)-4-methoxymethoxypiperidine.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. filtrationthe dilution was filtered
  3. customThe solvent in the filtrate was removed by distillation

Sources & evidence

ORD record
ord-b943896e0875473197f6767596198555
Source dataset
uspto-grants-1997_08
Patent number
US05658926

Reaction notes

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