Potassium Hydroxide → HCID 68708678, compound

HRID 645500Notes

Reaction equation

HRID 645500 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.[OH-].[K+].[CH3:19][N:20]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1>C1(C)C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CCOC(C)=O.O>[CH3:19][N:20]1[CH2:25][CH2:24][CH:23]([O:26][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=2)[CH2:22][CH2:21]1

Participants

8

Reactant 3

HCID 14797Potassium HydroxideHCID 660484-Piperidinol, 1-methyl-HCID 46314864HCID 46314864, compound

Product 1

HCID 68708678HCID 68708678, compound

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

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. extractionextracted with AcOEt (×2)
  2. dry with materialThe combined organic extracts are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel column chromatography (CH2Cl2:MeOH=10:1)

Sources & evidence

ORD record
ord-c586157e14c145d5a056585bb86d0211
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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