Sodium Hydroxide → HCID 58123840, compound

HRID 1616662Notes

Reaction equation

HRID 1616662 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[CH2:5][CH:6]1[C:11]([CH3:13])([CH3:12])[CH:10](O)[CH2:9][CH2:8][NH:7]1.[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[C:4]2[CH2:5][CH:6]3[C:11]([CH3:13])([CH3:12])[CH:10]([C:15]=2[CH:16]=[CH:17][CH:18]=1)[CH2:9][CH2:8][NH:7]3

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66942064HCID 66942064, compound

Product 1

HCID 58123840HCID 58123840, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 2-(2-methoxy-benzyl)-3,3-dimethyl-piperidin-4-ol (0.80 g) in polyphosphoric acid (10 mL) is stirred at 120° C. overnight. After cooling the solution to ca. 80° C., water (300 mL) is added and the mixture is stirred vigorously for another 10 min. Then, the mixture is cooled in an ice bath, more water is added, and the mixture is basified using 10 M aqueous NaOH solution. The resulting mixture is extracted with ethyl acetate, the combined organic extracts are washed with brine and dried (MgSO4). The solvent is removed under reduced pressure to yield the title product that is used without further purification.

Workup

  1. temperatureThen, the mixture is cooled in an ice bath
  2. extractionThe resulting mixture is extracted with ethyl acetate
  3. washthe combined organic extracts are washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-bd0e69fd9fb14eadaf59286b4fa3a46e
Source dataset
uspto-grants-2014_07
Patent number
US08765780B2

Reaction notes

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