Dabco → HCID 54363423, compound

HRID 1742469Notes

Reaction equation

HRID 1742469 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([OH:8])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14].N12CCN(CC1)CC2>C(Cl)Cl>[C:13](=[O:14])([O:8][CH:6]1[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3][C:2]([CH3:11])([CH3:1])[CH2:7]1)[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 9237Dabco2×HCID 15891Phenyl chloroformate2×HCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine2×

Product 1

HCID 54363423HCID 54363423, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 500 ml 3-neck flask was added 23.2 grams (0.14 mole) of 95% 2,2,6,6-tetramethyl-4-piperidinol and 400 ml of methylene chloride. The flask was equipped with a magnetic stirrer, thermometer, reflux condenser and dropping funnel containing 11.2 grams (0.07 mole) of phenyl chloroformate. The phenyl chloroformate was slowly added to the 2,2,6,6-tetramethyl-4-piperidinol solution without any appreciable exotherm. Then 0.5 grams of 1,4-diazabicyclo(2.2.2)octane (DABCO) was added at room temperature. The temperature rose to 35° C. and a precipitate formed. Another 0.5 gram of DABCO was added but no further exotherm occurred. After stirring for 11/2 hours, the solids were filtered off and the methylene chloride solution was washed with water, 10% NaOH and water again, dried over anhydrous MgSO4, filtered and the solvent stripped off on a rotating evaporator under reduced pressure. The residue was a white solid weighing 17.4 grams (90% crude yield) which had a melting point of 62°-65° C. Liquid chromatography indicated the product was essentially one component. The infrared spectrum contained a strong carbonyl peak at 1760 cm-1 and a moderate carbonyl peak at 1710 cm -1.

Workup

  1. customThe flask was equipped with a magnetic stirrer
  2. temperaturethermometer, reflux condenser
  3. customrose to 35° C.
  4. customa precipitate formed
  5. filtrationthe solids were filtered off
  6. washthe methylene chloride solution was washed with water, 10% NaOH and water again
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customthe solvent stripped off on a rotating evaporator under reduced pressure

Sources & evidence

ORD record
ord-4b6f405b6656402892f7ebcdd396f013
Source dataset
uspto-grants-1994_08
Patent number
US05338853

Reaction notes

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