3-Octanol → 1,3-Bis[N-n-octyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]cyclobutenediylium-2,4-diolate

HRID 485734

Reaction equation

HRID 485734 reaction equation
[CH2:1]([NH:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:20]1(O)[C:24](=[O:25])[C:22](=O)[C:21]=1[OH:26].[CH2:28]([CH:30](O)[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH3:29]>C1CCCCC1>[CH2:1]([N:9]([C+:20]1[C:21]([O-:26])=[C:22]([N:9]([CH:10]2[CH2:11][C:12]([CH3:19])([CH3:18])[NH:13][C:14]([CH3:17])([CH3:16])[CH2:15]2)[CH2:29][CH2:28][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C+:24]1[O-:25])[CH:10]1[CH2:11][C:12]([CH3:18])([CH3:19])[NH:13][C:14]([CH3:17])([CH3:16])[CH2:15]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 115273-OctanolHCID 17913Squaric acidHCID 143651212,2,6,6-Tetramethyl-4-octylaminopiperidine

Product 1

HCID 1784435941,3-Bis[N-n-octyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]cyclobutenediylium-2,4-diolateYield 84.4%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Under agitation, 339.6 g (1.26 moles) of 99.4% strength 4-n-octylamino-2,2,6,6-tetramethylpiperidine, 7.2 g (0.063 mole) of quadratic acid, and 150 cc of ethylhexanol was heated to boiling with reflux for 2.5 hours in a 1-liter stirred flask with water trap attached thereto; the solid matter was dissolved even before reaching reflux above 150° C. The sump temperature was 220° C. The amount of water removed from the cycle was 2.2 cc. Crystals precipitated from the reaction solution. After washing with petroleum ether and drying, 25.8 g was obtained. Yield: 84.4% of theory, mp 171°-175° C. (from cyclohexane). Extinction (g/l.cm) at 278 nm: 21; at 335 nm: 77.

Workup

  1. temperaturewith reflux for 2.5 hours in a 1-liter
  2. dissolutionthe solid matter was dissolved even
  3. temperaturebefore reaching reflux above 150° C
  4. customwas 220° C
  5. customThe amount of water removed from the cycle
  6. customCrystals precipitated from the reaction solution
  7. washAfter washing with petroleum ether
  8. customdrying
  9. custom25.8 g was obtained

Sources & evidence

ORD record
ord-cb9a5b0bd4ec4d619ed123b902c0d11c
Source dataset
uspto-grants-1985_08
Patent number
US04537924

Linked notes

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