Methyl iodide → 1-Benzyl-4-(N-methyl-N-(3-methoxymethyl-2-pyridyl)amino)piperidine

HRID 361805Notes

Reaction equation

HRID 361805 reaction equation
[OH-].[K+].[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]([CH3:25])[C:17]2[C:22]([CH2:23][OH:24])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:26]I>CS(C)=O.O>[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]([CH3:25])[C:17]2[C:22]([CH2:23][O:24][CH3:26])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:12][CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 106387941-Benzyl-4-(N-methyl-N-(3-hydroxymethyl-2-pyridyl)amino)piperidine

Product 1

HCID 108535171-Benzyl-4-(N-methyl-N-(3-methoxymethyl-2-pyridyl)amino)piperidine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To a mixture of powdered potassium hydroxide (356 mg) in dry dimethylsulfoxide (2 ml) under nitrogen is added a solution of 1-benzyl-4-(N-methyl-N-(3-hydroxymethyl-2-pyridyl)amino)piperidine (XXX, EXAMPLE 35, 494 mg) in dry dimethylsulfoxide (1.2 ml) followed by methyl iodide (118 μl). The resulting mixture is stirred at 20°-25° for 30 min and is then diluted with water (15 ml) and extracted with methylene chloride (2×20 ml). The combined organic phases are washed with water (2×10 ml) and saline (10 ml), dried over sodium sulfate and concentrated under reduced pressure to give a concentrate which is then chromatographed (silica gel, a gradient of ethyl acetate/hexane (20/80→40/60)) to give the title compound, NMR (CDCl3, 400 MHz) 8.22, 7.67, 7.31, 7.25, 6.89, 4.40, 3.50, 3.41, 3.28, 2.94, 2.77, 2.01, 1.86 and 1.70δ.

Workup

  1. extractionextracted with methylene chloride (2×20 ml)
  2. washThe combined organic phases are washed with water (2×10 ml) and saline (10 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give
  6. concentrationa concentrate which
  7. customis then chromatographed (silica gel

Sources & evidence

ORD record
ord-f51c07903c5c40a0a2ae9ef5ceef3212
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

Loading…