Water → 4-(4-bromo-1H-pyrazol-1-yl)-1-methylpiperidine

HRID 1627574Notes

Reaction equation

HRID 1627574 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=1.[CH3:13]CN(CC)CC.CI.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH:7]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 8471TriethylamineHCID 521916214-(4-Bromo-1H-pyrazol-1-yl)piperidine

Product 1

HCID 595994184-(4-bromo-1H-pyrazol-1-yl)-1-methylpiperidineYield 63.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-(4-bromo-pyrazol-1-yl)-piperidine (375 mg, 1.63 mmol) in DMF (3.26 mL) was added NEt3 (230 μL, 1.63 mmol) and stirred for 5 minutes. Methyliodide (MeI) (1.63 mL, 1M MeI in DMF, freshly made) was added and the reaction was stirred overnight at room temperature. Water was added and the solution was extracted with EtOAc (4×10 mL). The organic solution was washed with brine, dried with Na2SO4, concentrated, and dried in vacuo to afford 4-(4-bromo-pyrazol-1-yl)-1-methyl-piperidine (251 mg, 63% yield).

Workup

  1. additionwas added
  2. stirringthe reaction was stirred overnight at room temperature
  3. extractionthe solution was extracted with EtOAc (4×10 mL)
  4. washThe organic solution was washed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-5d70c6a2616543b4bcfbc9b6d830cfba
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

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