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

HRID 604415

Reaction equation

HRID 604415 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-ea043e40110f4b578f26c95c08e24e44
Source dataset
uspto-grants-2011_03
Patent number
US07910606B2

Linked notes

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