Potassium Carbonate → HCID 10711243, compound

HRID 361823Notes

Reaction equation

HRID 361823 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH3:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:15])[C:17]2[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 41361281-benzyl-N-methylpiperidin-4-amine

Product 1

HCID 10711243HCID 10711243, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-benzyl-4-methylaminopiperidine (EXAMPLE 9, 10.8 g), 2-chloro-3-nitropyridine (6.7 g) and anhydrous potassium carbonate (14.6 g) in dry acetonitrile (211 ml) is stirred under nitrogen at 20°-25° for 5 days. The mixture is then concentrated under reduced pressure, diluted with methylene chloride (200 ml) and water (50 ml), and the phases are separated. The organic phase is washed with saline (50 ml), dried over sodium sulfate and concentrated under reduced pressure to give the crude product which is then chromatographed (silica gel, 70-230 mesh, 100 g; eluting with ethyl acetate/hexane (50/50) to give the title compound, mp=92°-95°.

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure
  2. additiondiluted with methylene chloride (200 ml) and water (50 ml)
  3. customthe phases are separated
  4. washThe organic phase is washed with saline (50 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product which
  8. customis then chromatographed (silica gel, 70-230 mesh, 100 g
  9. washeluting with ethyl acetate/hexane (50/50)

Sources & evidence

ORD record
ord-a0dccd5828704152895a75e14acbd958
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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