Sodium Hydroxide → HCID 118323976, compound

HRID 1778315Notes

Reaction equation

HRID 1778315 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH:13]=[C:12]3[NH:20][CH:21]2[CH2:26][CH2:25][N:24](S(C(F)(F)F)(=O)=O)[CH2:23][CH2:22]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH:13]=[C:12]3[NH:20][CH:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride3×HCID 91844670HCID 91844670, compound

Product 1

HCID 118323976HCID 118323976, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 500-mL three-neck round bottom flask with stir bar, heating mantel, reflux condenser with N2 outlet, septa with N2 inlet (needle) and temperature probe was added 6-(bis(4-chlorophenyl)methyl)-4-(1-(trifluoromethylsulfonyl)piperidin-4-ylamino)quinolin-2(1H)-one (6.06 g; 9.93 mmol) and THF (120 mL). To this solution was added LAH (pellets, 1.48 g; 38.99 mmol) at room temperature and the resulting mixture was heated to reflux while stirring for 8 hr and cooled room temperature overnight. A 2nd charge of LAH (0.45 g; 11.86 mmol) was added and the resulting mixture was maintained at 60° C. for 6 hr. A 3rd charge of LAH (0.45 g; 11.86 mmol) was added and the resulting mixture was maintained at 60° C. for additional 3 h. The reaction was stopped and cooled to 0° C. with ice bath. Water (2.6 mL) (Note: highly exothermic) was added, then 15% NaOH (2.6 mL), then water (7.5 mL). The resulting mixture was stirred for 15 min and then Na2SO4 and THF was added. The reaction solution was filtered through CELITE. The filtrate was concentrated and the resulting solid residue was triturated with DCM (10 mL)/diethyl ether (25 mL) in an ice bath for 20 min to yield 6-(bis(4-chlorophenyl)methyl)-4-(piperidin-4-ylamino)quinolin-2(1H)-one as a pink solid.

Workup

  1. temperatureheating mantel
  2. temperaturereflux condenser with N2 outlet
  3. customsepta with N2 inlet
  4. temperaturethe resulting mixture was heated
  5. temperatureto reflux
  6. stirringwhile stirring for 8 hr
  7. additionwas added
  8. temperaturethe resulting mixture was maintained at 60° C. for 6 hr
  9. additionwas added
  10. temperaturethe resulting mixture was maintained at 60° C. for additional 3 h
  11. temperaturecooled to 0° C. with ice bath
  12. additionhighly exothermic) was added
  13. stirringThe resulting mixture was stirred for 15 min
  14. filtrationThe reaction solution was filtered through CELITE
  15. concentrationThe filtrate was concentrated
  16. customthe resulting solid residue was triturated with DCM (10 mL)/diethyl ether (25 mL) in an ice bath for 20 min

Sources & evidence

ORD record
ord-a03e49a3a8fd4e5c9efea5cd20667d39
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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