Tert-Butyl nitrite → HCID 12709388, compound

HRID 1265936Notes

Reaction equation

HRID 1265936 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]1([CH3:11])[CH3:10].N(OC(C)(C)C)=O.[CH2:19]([O:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1N)[CH:20]=[CH2:21]>N1C=CC=CC=1>[O:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[CH:20]([CH2:21][O:1][N:2]2[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]2([CH3:11])[CH3:10])[CH2:19]1

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 5499762,2,6,6-Tetramethylpiperidin-1-olHCID 64866392-(ALLYLOXY)ANILINE2×

Product 1

HCID 12709388HCID 12709388, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 1.95 g (12.5 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidine, 3.1 g (30 mmol) of tert-butyl nitrite and 7.5 mg (0.012 mmol) of (S,S)-(+)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) in 100 mL of pyridine at 65°-70° C. under a nitrogen atmosphere is added dropwise over 20 minutes a solution of 5.6 g (25 mmol) of 2-allyloxyaniline in 20 mL of pyridine. The evolution of gas is observed during the addition of the 2-allyloxyaniline. After the addition is complete, the reaction mixture is kept at 65°-70° C. for an additional forty minutes until gas evolution subsided. After cooling to ambient temperature, the reaction mixture is then concentrated. The residue obtained is purified by vacuum flash chromatography (heptane) to give 2.3 g of a viscous liquid in 63.7% yield. The structure is confirmed by 1Hnmr and elemental analyses.

Workup

  1. additionAfter the addition
  2. waitthe reaction mixture is kept at 65°-70° C. for an additional forty minutes until gas evolution
  3. concentrationthe reaction mixture is then concentrated
  4. customThe residue obtained
  5. customis purified by vacuum flash chromatography (heptane)

Sources & evidence

ORD record
ord-5a2ef82932344a8397a402a69881a41c
Source dataset
uspto-grants-2003_04
Patent number
US06547841B2

Reaction notes

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