Allyl bromide → 4-Allyloxy-2,2,6,6-tetramethylpiperidine hydrobromide

HRID 434456Notes

Reaction equation

HRID 434456 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([Br:18])C=C>CCOCC>[BrH:18].[CH2:1]([O:4][CH:5]1[CH2:6][C:7]([CH3:14])([CH3:13])[NH:8][C:9]([CH3:12])([CH3:11])[CH2:10]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 11117001Piperidine, 2,2,6,6-tetramethyl-4-(2-propen-1-yloxy)-

Product 1

HCID 197362214-Allyloxy-2,2,6,6-tetramethylpiperidine hydrobromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 9.87 parts of 4-allyloxy-2,2,6,6-tetramethylpiperidine and 3.03 parts of allyl bromide was heated at 90° C. for 96 hours. Ether was added to the cooled reaction mixture and the 4-allyloxy-2,2,6,6-tetramethylpiperidine hydrobromide formed during the reaction was filtered off. The ether solvent was removed by distillation under reduced pressure and the residue purified by chromatography to give 4-allyloxy-1-allyl-2,2,6,6-tetramethylpiperidine.

Sources & evidence

ORD record
ord-0c351d6a7d784c47934264b374a5a013
Source dataset
uspto-grants-1983_08
Patent number
USRE031343

Reaction notes

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