Pyridine → HCID 22598278, compound

HRID 1369350Notes

Reaction equation

[CH2:1]([N:5]([C:17]1[N:22]=[C:21]([N:23]([CH:28]2[CH2:33][C:32]([CH3:35])([CH3:34])[N:31]([OH:36])[C:30]([CH3:38])([CH3:37])[CH2:29]2)[CH2:24][CH2:25][CH2:26][CH3:27])[N:20]=[C:19]([N:39]([CH2:48][CH:49]([CH2:54][CH3:55])[CH2:50][CH2:51][CH2:52][CH3:53])[CH2:40][CH:41]([CH2:46][CH3:47])[CH2:42][CH2:43][CH2:44][CH3:45])[N:18]=1)[CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([OH:14])[C:8]([CH3:16])([CH3:15])[CH2:7]1)[CH2:2][CH2:3][CH3:4].N(O[C:59]([CH3:62])([CH3:61])C)=O.N[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1.N1C=C[CH:73]=[CH:72][CH:71]=1>>[CH2:24]([N:23]([C:21]1[N:22]=[C:17]([N:5]([CH:6]2[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([O:14][C:61]3[CH:59]=[CH:62][CH:73]=[CH:72][CH:71]=3)[C:8]([CH3:15])([CH3:16])[CH2:7]2)[CH2:1][CH2:2][CH2:3][CH3:4])[N:18]=[C:19]([N:39]([CH2:48][CH:49]([CH2:54][CH3:55])[CH2:50][CH2:51][CH2:52][CH3:53])[CH2:40][CH:41]([CH2:46][CH3:47])[CH2:42][CH2:43][CH2:44][CH3:45])[N:20]=1)[CH:28]1[CH2:29][C:30]([CH3:37])([CH3:38])[N:31]([O:36][C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[C:32]([CH3:34])([CH3:35])[CH2:33]1)[CH2:25][CH2:26][CH3:27]

Participants

Reactant 4

HCID 1049Pyridine

HCID 6115Aniline

HCID 10906Tert-Butyl nitrite

HCID 699644832,4-bis[N-butyl-N-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)amino]-6-[N,N-bis(2-ethylhexyl)amino]-s-triazine

Product 1

HCID 22598278HCID 22598278, compoundYield 83.3%

Procedure

The procedure of Example 1 is repeated using 5 g (6.5 mmol) of 2,4-bis[N-butyl-N-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)amino]-6-[N,N-bis(2-ethylhexyl)amino]-s-triazine, 3.09 g (30 mmol) of tert-butyl nitrite, 3.9 mg (0.0065 mmol) of (S,S)-(+)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II), 120 mL of pyridine and 2.42 g (26 mmol) of aniline at 75° C. The crude product obtained is purified by vacuum flash chromatography (2% ethyl acetate/heptane) to give 5 g of the title compound as a reddish oil in 83.3% yield. The structure is confirmed by 1Hnmr and elemental analysis.

Workup

customat 75° C
customThe crude product obtained
customis purified by vacuum flash chromatography (2% ethyl acetate/heptane)

Sources & evidence

ORD record: ord-298f9a37f47543efbcdf4407530e967c
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579328B2

Reaction notes

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