Aniline → 1-Phenoxy-2,2,6,6-tetramethylpiperidine

HRID 1760321Notes

Reaction equation

HRID 1760321 reaction equation
[CH3:1][C:2]1([CH3:11])[N:7]([O])[C:6]([CH3:10])([CH3:9])[CH2:5][CH2:4][CH2:3]1.[C:12]([O:16]N=O)(C)([CH3:14])[CH3:13].N[C:20]1[CH:25]=CC=C[CH:21]=1>N1C=CC=CC=1>[O:16]([N:7]1[C:2]([CH3:11])([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1([CH3:10])[CH3:9])[C:12]1[CH:14]=[CH:25][CH:20]=[CH:21][CH:13]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 10906Tert-Butyl nitriteHCID 2724126Tempo

Product 1

HCID 132131751-Phenoxy-2,2,6,6-tetramethylpiperidineYield 68.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The procedure of Example 5 is repeated using 1.95 g (12.5 mmol) of 2,2,6,6-tetramethylpiperidine-1-oxyl, 3.09 g (30.0 mmol) of tert-butylnitrite and 228 mg (˜0.125 mmol) of phosphomolydbic acid hydrate (H3PMo12O40) in 100 mL of pyridine and 2.32 g (25 mmol) of aniline in 5 mL of pyridine. The crude is purified by vacuum flash chromatography (heptane) to give 2.0 g of a colorless oil in 68.7% yield.

Workup

  1. customThe crude is purified by vacuum flash chromatography (heptane)

Sources & evidence

ORD record
ord-25742d98b81742f58c1cdf1e5d9bc33c
Source dataset
uspto-grants-2005_01
Patent number
US06841668B2

Reaction notes

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