Triethylamine → HCID 19003289, compound

HRID 2255728Notes

Reaction equation

HRID 2255728 reaction equation
Cl.[CH3:2][C:3]1([CH3:25])[CH2:8][CH:7]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][C:16]([C:19](Cl)=[O:20])=[CH:17][CH:18]=[C:11]3[C:10]2=[O:22])[CH2:6][C:5]([CH3:24])([CH3:23])[NH:4]1.[CH3:26][C:27]1([CH3:36])[CH2:32][CH:31]([OH:33])[CH2:30][C:29]([CH3:35])([CH3:34])[NH:28]1.C(N(CC)CC)C.[OH-].[Na+]>C(Cl)Cl.O.CN(C)C=O>[CH3:2][C:3]1([CH3:25])[CH2:8][CH:7]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][C:16]([C:19]([O:33][CH:31]4[CH2:32][C:27]([CH3:36])([CH3:26])[NH:28][C:29]([CH3:35])([CH3:34])[CH2:30]4)=[O:20])=[CH:17][CH:18]=[C:11]3[C:10]2=[O:22])[CH2:6][C:5]([CH3:24])([CH3:23])[NH:4]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidineHCID 131718103HCID 131718103, compound

Product 1

HCID 19003289HCID 19003289, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Into a 125 ml reaction flask equipped with a magnetic stirrer, thermometer, condenser and nitrogen atmosphere were placed 5.0 g (0.013 mol) of the acid chloride of Example 2 and 50 ml of 2% dimethylformamide in methylene chloride. This mixture was stirred during the addition of 2.1 g (0.013 mol) 2,2,6,6-tetramethyl-4-piperidinol and 2.8 g (0.028 mol) triethylamine. The reaction was then refluxed for 3 hours. The mixture was cooled and transferred to a separatory funnel with 100 ml methylene chloride, 25 ml water and 50 ml 5% sodium hydroxide. The mixture was shaken, allowed to separate and the organic phase drawn off. The aqueous phase (and interfacial solid) was extracted with an additional 25 ml solvent. The combined organic solutions were dried with anhydrous magnesium sulfate and the solvent stripped using aspirator vacuum. The product was 4.1 g of slightly yellow crystals (melting at 196°-200° C.). The infrared spectrum (chloroform) showed the carbonyl absorption at 1705 cm-1 (imide and ester). The NMR spectrum showed the anticipated aromatic ring (7.7-7.9 ppm, doublet, 1H; 8.3-8.5, multiplet, 2H) and two HALS groups [5.2-5.7 ppm, multiplet, 1H; 4.4-4.9 ppm, multiplet, 1H; 1.0-2.3 ppm, several multiplets including two singlets (1.2 and 1.3 ppm)]. The UV spectrum showed an absorbance maximum (THF) at 296 nm, molar absorptivity 300.

Workup

  1. customInto a 125 ml reaction flask
  2. customequipped with a magnetic stirrer
  3. customthermometer, condenser and nitrogen atmosphere were placed
  4. temperatureThe reaction was then refluxed for 3 hours
  5. temperatureThe mixture was cooled
  6. customto separate
  7. extractionThe aqueous phase (and interfacial solid) was extracted with an additional 25 ml solvent
  8. dry with materialThe combined organic solutions were dried with anhydrous magnesium sulfate
  9. customthe carbonyl absorption at 1705 cm-1 (imide and ester)

Sources & evidence

ORD record
ord-9dc225f1d2f8424c90241fb1453dd18f
Source dataset
uspto-grants-1993_08
Patent number
US05241067

Reaction notes

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