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Allyl bromide → 4-Allyloxy-1-octyloxy-2,2,6,6-tetramethylpiperidine

HRID 728100
Notes
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Reaction equation

HRID 728100 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[N:7]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:6]([CH3:22])([CH3:21])[CH2:5]1.[CH2:23](Br)[CH:24]=[CH2:25].CCCCCCC>O1CCCC1.C(OCC)(=O)C>[CH2:25]([O:3][CH:4]1[CH2:9][C:8]([CH3:10])([CH3:11])[N:7]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:6]([CH3:21])([CH3:22])[CH2:5]1)[CH:24]=[CH2:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 8900HeptaneHCID 24758Sodium hydrideHCID 113466831-Octyloxy-2,2,6,6-tetramethylpiperidin-4-ol

Product 1

HCID 233721064-Allyloxy-1-octyloxy-2,2,6,6-tetramethylpiperidineYield 70%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

Sodium hydride (2.65 grams, 110 mmol) is added to a solution of 30.0 grams (105 mmol) of 4-hydroxy-1-octyloxy-2,2,6,6-tetramethylpiperidine in 150 ml of tetrahydrofuran under nitrogen. The reaction mixture is heated at reflux for three hours, cooled to 35° C., and treated with 12.7 grams (110 mmol) of allyl bromide. The reaction mixture is heated at reflux for one hour, then partitioned between ethyl acetate (150 ml) and water (50 ml). The organic layer is washed with saturated sodium chloride solution (100 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is dissolved in heptane (50 ml) and passed through a pad of silica gel (eluent 5:1 heptane:ethyl acetate). The crude product is purified by flash chromatography (silica gel; 9:1 heptane:ethyl acetate to afford 23.9 grams (70% yield) of the title compound as a colorless oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for three hours
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux for one hour
  5. custompartitioned between ethyl acetate (150 ml) and water (50 ml)
  6. washThe organic layer is washed with saturated sodium chloride solution (100 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe residue is dissolved in heptane (50 ml)
  10. customThe crude product is purified by flash chromatography (silica gel

Sources & evidence

ORD record
ord-e9f82941fbbd405b8c17b0c59b1fc3e7
Source dataset
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05047489

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes