Triphenylphosphine → 1-methyl-4-(4-nitro-1H-pyrazol-1-yl)piperidine

HRID 1968522Notes

Reaction equation

HRID 1968522 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[CH3:9][N:10]1[CH2:15][CH2:14][CH:13](O)[CH2:12][CH2:11]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH3:9][N:10]1[CH2:15][CH2:14][CH:13]([N:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 163764-nitro-1H-pyrazoleHCID 660484-Piperidinol, 1-methyl-HCID 97268Di-tert-butyl azodicarboxylate

Product 1

HCID 670755081-methyl-4-(4-nitro-1H-pyrazol-1-yl)piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Nitro-1H-pyrazole (200 mg, 1.77 mmol), 1-methylpiperidin-4-ol (204 mg, 1.77 mmol) and triphenylphosphine (557 mg, 2.12 mmol) were combined in THF (6 mL) and di-tert-butyl azodicarboxylate (529 mg, 2.30 mmol) was added over about 1 minute. The resulting mixture was stirred at room temperature for 4 hours, and concentrated to dryness. The residue was purified by flash chromatography (Analogix, 12 g column, 0 to 7% methanol in CH2Cl2 over 25 minutes) to give 1-methyl-4-(4-nitro-1H-pyrazol-1-yl)piperidine.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was purified by flash chromatography (Analogix, 12 g column, 0 to 7% methanol in CH2Cl2 over 25 minutes)

Sources & evidence

ORD record
ord-7109c4401c5c4bc390e9bed7c4e7de1c
Source dataset
uspto-grants-2013_04
Patent number
US08426408B2

Reaction notes

Loading…