Carbonic acid, di-2-propen-1-yl ester → 2,2,6,6-Tetramethyl-1-(prop-2-en-1-yl)-4-[(prop-2-en-1-yl)oxy]piperidine

HRID 1199122Notes

Reaction equation

HRID 1199122 reaction equation
[CH2:1]([O:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[NH:8][C:7]([CH3:14])([CH3:13])[CH2:6]1)[CH:2]=[CH2:3].C(=O)(OCC=C)O[CH2:17][CH:18]=[CH2:19]>Cl[Pd]Cl>[CH2:19]([N:8]1[C:7]([CH3:14])([CH3:13])[CH2:6][CH:5]([O:4][CH2:1][CH:2]=[CH2:3])[CH2:10][C:9]1([CH3:12])[CH3:11])[CH:18]=[CH2:17]

Participants

4

Reactant 2

HCID 84764Carbonic acid, di-2-propen-1-yl esterHCID 11117001Piperidine, 2,2,6,6-tetramethyl-4-(2-propen-1-yloxy)-

Product 1

HCID 198681802,2,6,6-Tetramethyl-1-(prop-2-en-1-yl)-4-[(prop-2-en-1-yl)oxy]piperidineYield 63%

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Conditions

Temperature
110 °C

Procedure

4-allyloxy-2,2,6,6-tetramethyl-piperidine (150 g, 0.76 mol), di-allyl carbonate (115 g, 0.8 mol) and PdCl2 (1.35 g, 1.6 mmol) are charged under nitrogen atmosphere into a 3-necked 500 ml-flask equipped with a thermometer and a reflux condenser. The solution is heated under stirring to 110° C. for 24 hours. Gas-chromatographic analysis of the reaction mixture then shows that the reaction produced the desired 1-allyl-4-allyloxy-2,2,6,6-tetramethyl-piperidine in 63% yield (calculated on the starting 4-allyloxy-2,2,6,6-tetramethyl-piperidine) and >97% selectivity.

Workup

  1. customequipped with a thermometer and a reflux condenser
  2. temperatureThe solution is heated

Sources & evidence

ORD record
ord-ed69085a7ecc49bda8c0ecc5a67c49c9
Source dataset
uspto-grants-1990_02
Patent number
US04898946

Reaction notes

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