Sodium Hydroxide → HCID 58964257, compound

HRID 1362939Notes

Reaction equation

HRID 1362939 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH:22]C(=O)C)[CH:10]=[CH:11][C:12]=2[O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:5][CH:4]=[N:3]1.[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH2:22])[CH:10]=[CH:11][C:12]=2[O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:5][CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58964286HCID 58964286, compound

Product 1

HCID 58964257HCID 58964257, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

N-[3-(2-methyl-2H-pyrazol-3-yl)-4-(2-piperidin-1-yl-ethoxy)-phenyl]-acetamide (1.0 g, 2.92 mmol) was dissolved in ethanol (15 mL) then aqueous sodium hydroxide (2.5 mL, 50% w/w) was added and the reaction mixture stirred at 80° C. overnight then concentrated. Water and brine were added then extracted with EtOAc three times. The organic layers were combined, dried over anhydrous Na2SO4 then solvent removed under reduced pressure to afford 3-(2-methyl-2H-pyrazol-3-yl)-4-(2-piperidin-1-yl-ethoxy)-phenylamine as a brown oil in 97.1% yield.

Workup

  1. concentrationthen concentrated
  2. additionWater and brine were added
  3. extractionthen extracted with EtOAc three times
  4. dry with materialdried over anhydrous Na2SO4
  5. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-50ad1edeefa546baa21a1c9c3bc3942f
Source dataset
uspto-grants-2011_02
Patent number
US07884101B2

Reaction notes

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