HCID 68708678, compound → 5-[(1-Methyl-4-piperidinyl)oxy][1,1′-biphenyl]-2-amine

HRID 645501Notes

Reaction equation

HRID 645501 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)[CH2:4][CH2:3]1>CCO.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 68708678HCID 68708678, compound

Product 1

HCID 687052435-[(1-Methyl-4-piperidinyl)oxy][1,1′-biphenyl]-2-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-fluoro-2-nitrobiphenyl (0.86 mmol) in toluene/aq.KOH (2 mL/2 mL) are added 1-methylpiperidin-4-ol (1.1 mmol) and TBAB (0.17 mmol) at room temperature. After stirred at 70° C. overnight, the reaction mixture is diluted with AcOEt and water, and extracted with AcOEt (×2). The combined organic extracts are dried over Na2SO4, filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography (CH2Cl2:MeOH=10:1) to give 1-methyl-4-(6-nitrobiphenyl-3-yloxy)piperidine as a yellow solid. To a solution of 1-methyl-4-(6-nitrobiphenyl-3-yloxy)piperidine (0.63 mmol) in EtOH (5 mL) is added 5% palladium on activated carbon (50 mg) under N2 atmosphere. The reaction mixture is vigorously stirred at room temperature for 2.5 h under H2, and then filtered through celite (linsed with AcOEt). The filtrate is concentrated in vacuo to the title compound as a brown oil; 1H NMR (CDCl3), δ 1.79-1.87 (2H, m), 1.96-2.01 (2H, m), 2.25-2.31 (2H, m), 2.29 (3H, s), 2.70 (2H, brs), 3.52 (2H, m), 4.15-4.18 (1H, m), 6.70 (1H, d), 6.76-6.80 (2H, m), 7.32-7.38 (1H, m), 7.42-7.45 (4H, m).

Workup

  1. filtrationfiltered through celite (linsed with AcOEt)
  2. concentrationThe filtrate is concentrated in vacuo to the title compound as a brown oil

Sources & evidence

ORD record
ord-b6b1750616db42168d3d67481700f609
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

Loading…