Methyl iodide → 4-(4-bromo-1H-pyrazol-1-yl)-1-methylpiperidine

HRID 2400328Notes

Reaction equation

HRID 2400328 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.[CH2:13](N(CC)CC)C.CI>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

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 521916214-(4-Bromo-1H-pyrazol-1-yl)piperidine

Product 1

HCID 595994184-(4-bromo-1H-pyrazol-1-yl)-1-methylpiperidineYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-(4-bromopyrazol-1-yl)piperidine (480 mg, 2.09 mmol) and triethylamine (0.295 ml, 2.1 mmol) in DMF (4 ml) was added methyl iodide (2.1 ml of a 1.0M solution in DMF, 2.1 mmol) under an inert atmosphere. The reaction was stirred at room temperature overnight, then partitioned between water and EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give the product (260 mg), which was used without further purification. 1H NMR (400 MHz, CDCl3): 7.47 (1H, s), 7.45 (1H, s), 4.16-4.04 (1H, m), 3.09-2.92 (2H, m), 2.34 (3H, s), 2.30-2.10 (4H, m), 2.10-1.96 (2H, m).

Workup

  1. custompartitioned between water and EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2026211a49684f48abf8970d1e018ef3
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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