Pyridine → HCID 69964938, compound

HRID 1369355Notes

Reaction equation

[C:1]([O:25][CH:26]1[CH2:31][C:30]([CH3:33])([CH3:32])[N:29]([OH:34])[C:28]([CH3:36])([CH3:35])[CH2:27]1)(=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:18][C:17]([CH3:20])([CH3:19])[N:16]([OH:21])[C:15]([CH3:23])([CH3:22])[CH2:14]1)=[O:11].N(O[C:40]([CH3:43])([CH3:42])C)=O.N[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.N1C=C[CH:54]=[CH:53][CH:52]=1>>[C:1]([O:25][CH:26]1[CH2:27][C:28]([CH3:36])([CH3:35])[N:29]([O:34][C:42]2[CH:40]=[CH:43][CH:54]=[CH:53][CH:52]=2)[C:30]([CH3:33])([CH3:32])[CH2:31]1)(=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:14][C:15]([CH3:22])([CH3:23])[N:16]([O:21][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:17]([CH3:19])([CH3:20])[CH2:18]1)=[O:11]

Participants

Reactant 4

HCID 1049Pyridine

HCID 6115Aniline

HCID 10906Tert-Butyl nitrite

HCID 11272241Bis(1-hydroxy-2,2,6,6-tetramethyl-4-piperidinyl)decandioate

Product 1

HCID 69964938HCID 69964938, compoundYield 47.9%

Procedure

The procedure of Example 1 is repeated using 23.32 g (240 mmol) of bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 30.9 g (300 mmol) of tert-butyl nitrite, 35.5 mg (0.059 mmol) of (S,S)-(+)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II), 120 mL of pyridine and 22.32 g (240 mmol) of aniline at 70° C. A total of 10 g of the 47 g of crude product is purified by vacuum flash chromatography (1% ethyl acetate in heptane) to give 4.0 g of the title compound as a yellowish solid in 47.9% yield. The structure is confirmed by 1Hnmr, elemental and mass spectrographic analyses.

Workup

customat 70° C
customA total of 10 g of the 47 g of crude product is purified by vacuum flash chromatography (1% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-26689a1f020341d88856653997c11941
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579328B2

Reaction notes

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