4-Chloropyridine → tert-Butyl [1-(pyridin-4-yl)piperidin-4-yl]carbamate

HRID 33241

Reaction equation

HRID 33241 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1>C(O)CCC.O.CCN(CC)CC.C(Cl)Cl>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 122884-ChloropyridineHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 18008972tert-Butyl [1-(pyridin-4-yl)piperidin-4-yl]carbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 86625244n-butanol water NEt3Solvent

Procedure

A solution of 3 g Piperidin-4-yl-carbamic acid tert-butyl ester and 2.5 g 4-Chloropyridine in 9 ml n-butanol/water/NEt3 1:1:1 was heated at 100° C. for 48 h. Then the solution was cooled to RT diluted with DCM and washed with NaHCO3 solution and water. The organic layer was dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Chromatographic purification of the residue on silica with DCM as eluent gave after evaporation of the fractions containing the product a white foam. Yield 1.7 g.

Workup

  1. washwashed with NaHCO3 solution and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customChromatographic purification of the residue on silica with DCM as eluent
  6. customgave
  7. customafter evaporation of the fractions
  8. additioncontaining the product a white foam

Sources & evidence

ORD record
ord-67cb0225ae7f4dc89bfb109598d6f565
Source dataset
uspto-grants-2008_09
Patent number
US07429581B2

Linked notes

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