Piperidine → HCID 12490572, compound

HRID 1855440Notes

Reaction equation

HRID 1855440 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([CH3:9])[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[N:7]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 794712,4-Dichloro-6-methylpyrimidine

Product 1

HCID 12490572HCID 12490572, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichloro-6-methylpyrimidine (998 mg, 6.0 mmol) in tetrahydrofurane (30 mL) was added under stirring N,N-diisopropyl ethyl amine (853 mg, 6.6 mmol) and piperidine (613 mg, 6.6 mmol) and the reaction was stirred over night at 20° C. The solvent was evaporated under reduced pressure and the residue was taken up in water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure to dryness. The residue was purified by column chromatography on silica gel using heptane/ethyl acetate (9:1 to 7:3 v/v) as eluent to yield the title compound (678 mg, 53%) as light yellow crystals. MS ISP (m/e): 212.1/214.3 (100/40) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=6.70 (s, 1H), 3.58 (m, 4H), 2.22 (s, 3H), 1.61 (m, 2H), 1.51 (m, 4H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure to dryness
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-58e846ce0aca4e1396328a4bc9ef57ae
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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