1-Benzyl-4-[N-methyl-N-(3-(1-ethoxycyclopropylamino)-2-pyridinyl)amino]piperidine → 1-Benzyl-4-[N-methyl-N-(3-(1-methylcyclopropylamino)-2-pyridinyl)amino]piperidine

HRID 361826Notes

Reaction equation

HRID 361826 reaction equation
[Br-].[Li+].[CH3:3][Li].[CH2:5]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]([CH3:32])[C:19]2[C:24]([NH:25][C:26]3(OCC)[CH2:28][CH2:27]3)=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[CH2:5]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]([CH3:32])[C:19]2[C:24]([NH:25][C:26]3([CH3:3])[CH2:27][CH2:28]3)=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 106435211-Benzyl-4-[N-methyl-N-(3-(1-ethoxycyclopropylamino)-2-pyridinyl)amino]piperidineHCID 178419607HCID 178419607, compound

Product 1

HCID 105698881-Benzyl-4-[N-methyl-N-(3-(1-methylcyclopropylamino)-2-pyridinyl)amino]piperidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a mixture of methyllithium-lithium bromide (1.5M in ether, 2.28 ml) in dry toluene (6.3 ml) at -78° under nitrogen in a flame-dried flask is added a mixture of 1-benzyl-4-[N-methyl-N-(3-(1-ethoxycyclopropylamino)-2-pyridinyl)amino]piperidine (EXAMPLE 123, 325 mg) in dry toluene (8.5 ml) at -78°. The mixture is stirred at -78° C. for 1 hr, quenched carefully with saturated aqueous ammonium chloride (10 ml) and water (10 ml) and warmed to 20°-25°. The mixture is extracted with ethyl acetate (25 ml) and the organic phase is washed with water (10 ml) and saline (10 ml), dried over magnesium sulfate and concentrated to give the crude product which is chromatographed (silica gel, 230-400 mesh, 35 g; eluting with a gradient of methanol/chloroform (1/99-4/96)) to give the title compound, NMR (CDCl3) 7.72, 7.31, 7.25, 7.17, 6.91, 5.02, 3.50, 3.02, 2.88, 2.59, 2.01, 1.71, 1.32, 0.75 and 0.65δ.

Workup

  1. additionis added
  2. customquenched carefully with saturated aqueous ammonium chloride (10 ml) and water (10 ml)
  3. temperaturewarmed to 20°-25°
  4. extractionThe mixture is extracted with ethyl acetate (25 ml)
  5. washthe organic phase is washed with water (10 ml) and saline (10 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give the crude product which
  9. customis chromatographed (silica gel, 230-400 mesh, 35 g
  10. washeluting with a gradient of methanol/chloroform (1/99-4/96))

Sources & evidence

ORD record
ord-efcdc2badada4f4a93e08e5709781ac5
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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