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

HRID 1925392Notes

Reaction equation

HRID 1925392 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[CH:9]=[C:10]([NH2:18])[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=2)[CH2:4][CH2:3]1>CCO>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([C:8]2[CH:9]=[C:10]([NH2:18])[CH:11]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 1

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

Product 1

HCID 219593793-(1-Methylpiperidin-4-yl)-5-(trifluoromethyl)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 100 mL round bottom flask was placed 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(trifluoromethyl)benzenamine (2.05 g, 8 mmol) and EtOH (40 mL). Flask sparged with argon, then 10% Palladium on carbon (100 mg) is added. Argon removed and replaced with hydrogen via balloon, stirs overnight at RT. Work up: Filtered reaction mixture through Celite® under inert atmosphere. Removed solvents under reduced pressure. Purified via silica column using 0 to 100% 90/10/1 (DCM/MeOHINH4OH) gradient in DCM. Affords a pale yellow oil. LC-MS (+) shows mass 259 (M+H), as expected for C13H17F3N2, mw 258.28.

Workup

  1. customInto a 100 mL round bottom flask was placed
  2. customFlask sparged with argon
  3. addition10% Palladium on carbon (100 mg) is added
  4. customArgon removed
  5. customreplaced with hydrogen via balloon, stirs overnight at RT
  6. filtrationFiltered
  7. customreaction mixture through Celite® under inert atmosphere
  8. customPurified via silica column
  9. customAffords a pale yellow oil

Sources & evidence

ORD record
ord-adf80e7e8b3040bdbe0620b6d94bbb0f
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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