Water → 3-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(trifluoromethyl)benzenamine

HRID 2115886Notes

Reaction equation

HRID 2115886 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1[CH:9]=[C:10]([C:18]2[CH2:23][CH2:22][N:21]([C:24](OC(C)(C)C)=O)[CH2:20][CH:19]=2)[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1.O.[OH-].[Na+]>C1COCC1>[CH3:24][N:21]1[CH2:20][CH:19]=[C:18]([C:10]2[CH:9]=[C:8]([NH2:7])[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:11]=2)[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 67520234tert-butyl 4-(3-amino-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 219596433-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(trifluoromethyl)benzenamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 100 mL round bottom flask was placed LAH (1.518 g, 40 mmol) and suspended in THF (30 mL). Flask placed into an ice bath. Tert-butyl 4-(3-amino-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (1.368 g, 4 mmol) is added to THF (10 mL) and this solution is in turn added dropwise to the LAH suspension at 0° C. 15 min after addition was complete, flask is equipped with reflux condensor and allowed to reflux 15 h with stirring. Work up: Water (1.5 g) is added dropwise, then 15% NaOH(aq)(w/w)(1.5 g), followed by water (3 g). White precipitate forms after 20 h of stirring, filtered solids, removed solvent under reduced pressure. No further purification done. LC-MS(+) shows mass 257 (M+H), as expected for C13H15F3N2, mw 256.27.

Workup

  1. customInto a 100 mL round bottom flask was placed
  2. customFlask placed into an ice bath
  3. addition15 min after addition
  4. customflask is equipped
  5. temperaturewith reflux condensor
  6. temperatureto reflux 15 h
  7. stirringWhite precipitate forms after 20 h of stirring
  8. filtrationfiltered solids
  9. customremoved solvent under reduced pressure
  10. customNo further purification

Sources & evidence

ORD record
ord-83dd7d3623b04959990e518d466c4a7a
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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