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

HRID 1720296Notes

Reaction equation

HRID 1720296 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-].[K+].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 962WaterHCID 14797Potassium HydroxideHCID 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 potassium 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-c3ad9d8cfb27477b9f7d01af74960ffe
Source dataset
uspto-grants-1996_04
Patent number
US05506239

Reaction notes

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