Lithium Hydroxide → HCID 66649821, compound

HRID 419565Notes

Reaction equation

HRID 419565 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[NH:22]C(=O)C(F)(F)F)[CH3:2].[Li+].[OH-]>C1COCC1.O>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[NH2:22])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 86625198HCID 86625198, compound

Product 1

HCID 66649821HCID 66649821, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To N-(2-(ethyloxy)-4-{1-[2-(methylsulfonyl)ethyl]-4-piperidinyl}phenyl)-2,2,2-trifluoroacetamide (1.4 g, 3.3 mmol) in THF (25 mL) and H2O (25 mL) was added LiOH (0.21 g, 5.0 mmol). The mixture was stirred for two h and then more LiOH (0.21 g, 5.0 mmol) was added. After stirring for one h, the product was extracted with EtOAc. The organic layer was dried (MgSO4), filtered and rotovaped to provided the title compound of step G as a colorless oil (1.0 g, 3.1 mmol, 94%). 1H NMR (400 MHz, DMSO-d6) δ 6.66-6.56 (m, 3H), 4.02 (q, J=7.0 Hz, 2H), 3.15 (t, J=6.6 Hz, 2H), 3.03 (s, 3H), 2.99 (d, J=11.5 Hz, 2H), 2.88 (t, J=6.6 Hz, 2H), 2.42-2.32 (m, 1H), 2.13 (dd, J=11.9, 11.7 Hz, 2H), 1.82 (d, J=13.0 Hz, 2H), 1.70-1.58 (m, 2H), 1.39 (t, J=7.0 Hz, 3H).

Workup

  1. stirringAfter stirring for one h
  2. extractionthe product was extracted with EtOAc
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-53f7f77034604b82bc168e87ecffbc4e
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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