Sodium Hydroxide → HCID 22021951, compound

HRID 1793446Notes

Reaction equation

HRID 1793446 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[NH:8]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.O>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([CH:9]2[NH:8][CH:7]([CH2:5][NH:4][CH2:3][CH2:2][OH:1])[CH2:12][CH2:11][CH2:10]2)[CH:18]=[CH:17][C:16]=1[O:19][CH3:20]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 86597235HCID 86597235, compound

Product 1

HCID 22021951HCID 22021951, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 1.5 g (5.0 mmoles, 1 eq) of 6-(3,4-Dimethoxy-phenyl)-piperidine-2-carboxylic acid (2-hydroxy-ethyl)-amide in 18 mL of THF is added slowly into 15 mL of 1 M LiAlH4 solution in THF. The reaction is heated at 60° C. under N2 for 6 hours. At that time there is no starting material shown on TLC. Cooled in ice bath, to the reaction are added 0.5 ml water, 0.5 mL 15% NaOH and 1.5 mL water slowly in order. Finally, some anhydrous MgSO4 is added, and the reaction mixture is filtered through Celite. Upon the removal of the solvent, the residue is taken in ethyl acetate, washed with brine, dried over Na2SO4 and concentrated to afford 2-{[6-(3,4-dimethoxy-phenyl)-piperidin-2-ylmethyl]-amino}-ethanol as an oil (1.5 g, 68%), which is used in the next step without purification. Analysis: MS (LC-MS): Calculated for C16H26N2O3 294.39, found 295.37 (M+1).

Workup

  1. temperatureCooled in ice bath
  2. filtrationthe reaction mixture is filtered through Celite
  3. customUpon the removal of the solvent
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ba9af9d5a2b5441a870843b3f061c6cf
Source dataset
uspto-grants-2006_07
Patent number
US07081458B2

Reaction notes

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