1-(2-Fluoroethyl)-4-[3-(methyloxy)-4-nitrophenyl]-1,2,3,6-tetrahydropyridine → 4-[1-(2-Fluoroethyl)-4-piperidinyl]-2-(methyloxy)aniline

HRID 419556Notes

Reaction equation

HRID 419556 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([O:19][CH3:20])[CH:11]=2)[CH2:6][CH2:5]1>CCOC(C)=O.[Pd]>[F:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([O:19][CH3:20])[CH:11]=2)[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 594528351-(2-Fluoroethyl)-4-[3-(methyloxy)-4-nitrophenyl]-1,2,3,6-tetrahydropyridine

Product 1

HCID 594527574-[1-(2-Fluoroethyl)-4-piperidinyl]-2-(methyloxy)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 1-(2-fluoroethyl)-4-[3-(methyloxy)-4-nitrophenyl]-1,2,3,6-tetrahydropyridine (0.90 g, 3.2 mmol) in EtOAc (20 mL) was added Pd (10%) on carbon (100 mg). The reaction was evacuated then refilled with 10 psi H2 gas. The reaction was stirred for 3 days. The reaction was evacuated and the atmosphere replaced with N2. The solution was filtered to remove Pd/carbon and rotovaped down to give the title compound of step C as a red crystalline solid (800 mg, 3.2 mmol, 100% yield). 1H NMR (400 MHz, CDCl3) δ 6.69 (s, 1H), 6.66-6.64 (m, 2H), 4.70 (dd, J=5.1, 4.8 Hz, 1H), 4.58 (dd, J=5.1, 4.81 Hz, 1H), 3.83 (s, 3H), 3.69 (brs, 2H), 3.17-3.05 (m, 2H), 2.84-2.72 (m, 2H), 2.48-2.36 (m, 1H), 2.27-2.14 (m, 2H), 1.92-1.79 (m, 4H).

Workup

  1. customThe reaction was evacuated
  2. additionthen refilled with 10 psi H2 gas
  3. customThe reaction was evacuated
  4. filtrationThe solution was filtered
  5. customto remove Pd/carbon

Sources & evidence

ORD record
ord-02b71404b53e48a6b1f59700d04dbd5d
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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