Squaric acid → HCID 178456803, compound

HRID 485732

Reaction equation

HRID 485732 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[NH:8][C:7]([CH3:14])([CH3:13])[CH2:6]1)[CH2:2][CH3:3].[C:15]1(O)[C:19](=[O:20])[C:17](=O)[C:16]=1[OH:21]>C(C(O)CCCCC)C>[CH2:1]([N:4]([C+:15]1[C:16]([O-:21])=[C:17]([N:4]([CH:5]2[CH2:6][C:7]([CH3:14])([CH3:13])[NH:8][C:9]([CH3:11])([CH3:12])[CH2:10]2)[CH2:1][CH2:2][CH3:3])[C+:19]1[O-:20])[CH:5]1[CH2:6][C:7]([CH3:13])([CH3:14])[NH:8][C:9]([CH3:12])([CH3:11])[CH2:10]1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 17913Squaric acidHCID 15165090Propyl-(2,2,6,6-tetramethyl-piperidin-4-YL)-amine

Product 1

HCID 178456803HCID 178456803, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 115273-OctanolSolvent

Procedure

Under agitation, 363.0 g (1.83 moles) of 4-n-propylamino-2,2,6,6-tetramethylpiperidine, 10.8 g (0.095 mole) of quadratic acid, and 150 cc of ethylhexanol were heated in a 1-liter agitated flask with attached water trap for five hours under reflux to boiling; the sump temperature was 205° C., and 3.0 cc of water was removed from the cycle. After concentration of the reaction solution, 33.9 g of crystals was precipitated. Yield: 75.2%, mp 198°-199° C. (from cyclohexane). Extinction (g/l.cm) at 278 nm: 27; at 335 nm: 95.

Workup

  1. temperatureunder reflux to boiling
  2. customwas 205° C.
  3. custom3.0 cc of water was removed from the cycle
  4. customAfter concentration of the reaction solution, 33.9 g of crystals was precipitated

Sources & evidence

ORD record
ord-e0407b1571c7404d98d81453d3f76ce6
Source dataset
uspto-grants-1985_08
Patent number
US04537924

Linked notes

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