Piperidine → 5-Bromo-2-(piperidin-1-yl)pyrimidine

HRID 222652Notes

Reaction equation

HRID 222652 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:9]=[N:10][C:11](Cl)=[N:12][CH:13]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:7][C:8]1[CH:9]=[N:10][C:11]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:12][CH:13]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 36146825-Bromo-2-(piperidin-1-yl)pyrimidine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Piperidine (5.1 ml, 51.6 mmol) was added to a stirred solution of 5-bromo-2-chloropyrimidine (5 g, 25.8 mmol) and triethylamine (9.0 ml, 64.5 mmol) in toluene (30 ml). After stirring at room temperature for 24 hours the reaction mixture was diluted with ethyl acetate and washed with 2N hydrochloric acid, brine and dried (magnesium sulfate). The organic layer was filtered, concentrated in vacuo and the resulting residue was purified by column chromatography eluting with ethyl acetate to afford the title compound (D32).

Workup

  1. washwashed with 2N hydrochloric acid, brine
  2. dry with materialdried (magnesium sulfate)
  3. filtrationThe organic layer was filtered
  4. concentrationconcentrated in vacuo
  5. customthe resulting residue was purified by column chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-56ca97eabe37413bb9a2f7c963a16479
Source dataset
uspto-grants-2012_06
Patent number
US08207331B2

Reaction notes

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