Hydrochloric Acid → HCID 19073317, compound

HRID 1955964Notes

Reaction equation

HRID 1955964 reaction equation
[CH2:1]([NH:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[NH:9][C:8]([CH3:15])([CH3:14])[CH2:7]1)[CH2:2][CH2:3][CH3:4].CCC1OC2C=CC(N)=C[C:22]=2[C:20](=[O:21])N1.Cl.[CH2:31]1[O:33][CH2:32]1>CO>[CH2:1]([N:5]([CH:6]1[CH2:7][C:8]([CH3:14])([CH3:15])[N:9]([CH2:31][CH2:32][OH:33])[C:10]([CH3:13])([CH3:12])[CH2:11]1)[CH2:22][CH2:20][OH:21])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6354Ethylene OxideHCID 3726335793-87-4HCID 118285n-Butyl-2,2,6,6-tetramethyl-4-piperidinamine

Product 1

HCID 19073317HCID 19073317, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A steel autoclave is charged with 42.47 g (0.20 mol) of 4-n-butylamino-2,2,6,6-tetramethylpiperidine [EP-A-302 020, Example 1, page 4], 3 ml of concentrated hydrochloric acid and 300 ml of methanol. The autoclave is blanketed with nitrogen. 26.5 g (0.60 mol) of ethylene oxide are then introduced under pressure and the entire reaction mixture is heated to 150° C. The pressure in the autoclave is 10 bar. After 30 hours the reaction mixture is cooled to room temperature. About 250 ml of methanol are distilled off and the residue is poured into an aqueous saturated solution of sodium hydrogen carbonate and extracted three times with ethyl acetate. The organic phases are washed with an aqueous solution of saturated sodium chloride, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Chromatography of the residue over silica gel using the solvent system hexane/ethyl acetate 3:1 to 1:1 and ethyl acetate gives 31.5 g (53%) of 2-(n-butyl-[1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine-4-yl]amino)ethanol (compound (202)) in the form of a pale yellow oil.

Workup

  1. customthe entire reaction mixture
  2. temperatureAfter 30 hours the reaction mixture is cooled to room temperature
  3. distillationAbout 250 ml of methanol are distilled off
  4. additionthe residue is poured into an aqueous saturated solution of sodium hydrogen carbonate
  5. extractionextracted three times with ethyl acetate
  6. washThe organic phases are washed with an aqueous solution of saturated sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated on a vacuum rotary evaporator

Sources & evidence

ORD record
ord-3d5f1a722a964c26922de9b46af6a203
Source dataset
uspto-grants-1998_07
Patent number
US05777113

Reaction notes

Loading…