Pyridine → HCID 12709388, compound

HRID 1265938Notes

Reaction equation

HRID 1265938 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5](O)[CH2:4][C:3]1([CH3:12])[CH3:11].N(OC(C)(C)C)=O.N1C=CC=CC=1.[CH2:26]([O:29][C:30]1[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=1N)[CH:27]=[CH2:28]>ClC1C=CC=CC=1>[O:29]1[C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[CH:27]([CH2:28][O:1][N:2]2[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]2([CH3:12])[CH3:11])[CH2:26]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 10906Tert-Butyl nitriteHCID 64866392-(ALLYLOXY)ANILINE

Product 1

HCID 12709388HCID 12709388, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

The procedure of Example 1 is repeated using 1.95 g (12.5 mmol) of 1-oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidine, 3.10 g (30 mmol) of tert-butyl nitrite, 2.4 g (25 mmol) of pyridine, 7.5 mg (0.012 mmol) of (S,S)-(+)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) mmol) in 100 mL of chlorobenzene and 5.60 g (25 mmol) of 2-allyloxyaniline in 20 mL of chlorobenzene. The crude product obtained is purified by vacuum flash chromatography (25% ethyl acetate/heptane) to give 2.13 g of a viscous liquid in 59.0% yield.

Workup

  1. customThe crude product obtained
  2. customis purified by vacuum flash chromatography (25% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-79dbba16729b48d0a453692619b99e10
Source dataset
uspto-grants-2003_04
Patent number
US06547841B2

Reaction notes

Loading…