1-Methyl-4-(methylamino)piperidine → 3-[4-(4-Nitrophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)urea

HRID 492757Notes

Reaction equation

HRID 492757 reaction equation
C1(O[C:8](=[O:26])[NH:9][C:10]2[CH:15]=[C:14]([O:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=3)[CH:13]=[CH:12][N:11]=2)C=CC=CC=1.[CH3:27][NH:28][CH:29]1[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]1>CN(C)C=O>[N+:23]([C:20]1[CH:19]=[CH:18][C:17]([O:16][C:14]2[CH:13]=[CH:12][N:11]=[C:10]([NH:9][C:8](=[O:26])[N:28]([CH3:27])[CH:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)[CH:15]=2)=[CH:22][CH:21]=1)([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 5663231-Methyl-4-(methylamino)piperidineHCID 57677544[4-(4-Nitrophenoxy)pyridin-2-yl]carbamic acid phenyl ester

Product 1

HCID 231533743-[4-(4-Nitrophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)ureaYield 21,051%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[4-(4-Nitrophenoxy)pyridin-2-yl]carbamic acid phenyl ester (150 mg) was dissolved in N,N-dimethylformamide (4 ml) under a nitrogen atmosphere, and then N-methyl-N-(1-methylpiperidin-4-yl)amine (0.186 mg) was added thereto, followed by stirring for 1 hr. The reaction mixture was partitioned between ethyl acetate (40 ml) and a saturated aqueous solution of ammonium chloride (10 ml). The organic layer was washed with a saturated aqueous solution of ammonium chloride, water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; heptane:ethyl acetate=1:1, then ethyl acetate). Fractions containing the target compound were concentrated under a reduced pressure to provide 3-[4-(4-nitrophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)urea (117.7 mg, 71.5%) as a crude product.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (40 ml)
  2. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride, water and brine in this order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under a reduced pressure
  5. customto give a residue, which
  6. customwas then purified by silica gel column chromatography (Fuji Silysia NH, eluent
  7. additionFractions containing the target compound
  8. concentrationwere concentrated under a reduced pressure

Sources & evidence

ORD record
ord-b8c20e549e7142f1bf23d22a103972c9
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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