4-Hydroxy-2,2,6,6-tetramethylpiperidine → HCID 19073315, compound

HRID 1955969Notes

Reaction equation

HRID 1955969 reaction equation
[OH:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[NH:5][C:4]([CH3:11])([CH3:10])[CH2:3]1>C(#N)C>[OH:1][CH:2]1[CH2:3][C:4]([CH3:11])([CH3:10])[N:5]([CH2:7][C:2]#[C:3][CH2:4][N:5]2[C:6]([CH3:9])([CH3:8])[CH2:7][CH:2]([OH:1])[CH2:3][C:4]2([CH3:11])[CH3:10])[C:6]([CH3:9])([CH3:8])[CH2:7]1

Participants

3

Reactant 1

HCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 19073315HCID 19073315, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A round-bottomed flask, equipped with magnetic stirrer and condenser, is charged with 833 g (5.30 mol) of 4-hydroxy-2,2,6,6-tetramethylpiperidine and 418 g (1.05 mol) of 2-butyne-1,4-diol-ditosylate [C.A. Registry No. 6337-59-3] in 3.6 1 of acetonitrile under argon. The reaction mixture is refluxed overnight, then cooled, poured on ice and extracted repeatedly with ethyl acetate. The organic phases are combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Crystallisation of the residue from ethanol gives 295 g (76%) of 1,4-bis(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)but-2-yne (209), m.p. 203.4° C., in the form of white crystals.

Workup

  1. customA round-bottomed flask, equipped with magnetic stirrer and condenser
  2. temperatureThe reaction mixture is refluxed overnight
  3. temperaturecooled
  4. additionpoured on ice
  5. extractionextracted repeatedly with ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated on a vacuum rotary evaporator
  8. customCrystallisation of the residue from ethanol

Sources & evidence

ORD record
ord-49a225bfa58c4ad49260d26b1e97ff49
Source dataset
uspto-grants-1998_07
Patent number
US05777113

Reaction notes

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