3-Methylpiperidine → 3-methyl-1-(4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)piperidine

HRID 1466618Notes

Reaction equation

HRID 1466618 reaction equation
Cl[C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[N:5]=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[CH3:18][CH:19]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]1>C(O)CCC>[CH3:18][CH:19]1[CH2:24][CH2:23][CH2:22][N:21]([C:2]2[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[N:5]=[CH:4][C:3]=2[N+:15]([O-:17])=[O:16])[CH2:20]1

Participants

4

Reactant 2

HCID 790813-MethylpiperidineHCID 66850827HCID 66850827, compound

Product 1

HCID 668505613-methyl-1-(4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)piperidineYield 113.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 5-chloro-4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (348.3 mg, 1.254 mmol) in 1 mL n-butanol was added 3-methyl-piperidine (0.20 mL, 1.7 mmol). The reaction mixture was subjected to microwave irradiation at a temperature of 120° C. for 30 minutes. The solvent was evaporated in vacuo and the crude product purified via flash chromatography on silica gel (0 to 40% ethyl acetate in heptanes) to yield 486.5 mg of 3-methyl-1-(4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)piperidine. LCMS (ESI) m+H=341.4; 1H NMR (400 MHz, DMSO-d6) δ: 8.04 (s, 1H), 5.36 (s, 2H), 3.71-3.62 (m, 2H), 3.20 (m, 3H), 2.96-2.85 (m, 1H), 1.84-1.76 (m, 4H), 1.15 (m, 1H), 0.97-0.87 (m, 5H), 0.00 (s, 9H).

Workup

  1. customirradiation at a temperature of 120° C. for 30 minutes
  2. customThe solvent was evaporated in vacuo
  3. customthe crude product purified via flash chromatography on silica gel (0 to 40% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-166e100937854ba19942c6adbb57c741
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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