Sodium Hydroxide → HCID 58964257, compound

HRID 1626164Notes

Reaction equation

HRID 1626164 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-33fb3e5f6aed43b8a4799d8a6278cce3
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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