Piperidine → 2,5-Dimethyl-6-piperidinohex-4-en-2-ol

HRID 46802

Reaction equation

HRID 46802 reaction equation
Br[C:2]([CH3:4])=[CH2:3].[CH3:5][C:6]([OH:10])([CH:8]=[CH2:9])[CH3:7].[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:5][C:6]([OH:10])([CH2:8][CH:9]=[C:2]([CH3:4])[CH2:3][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:7]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 82572-Methyl-3-buten-2-olHCID 112022-BromopropeneHCID 11776Triphenylphosphine

Product 1

HCID 540736012,5-Dimethyl-6-piperidinohex-4-en-2-olYield 80%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 10 mmoles 2-bromopropene, 12.5 mmoles 2-methyl-3-buten-2-ol, 30 mmoles piperidine, 0.10 mmole palladium acetate and 0.20 mmole triphenylphosphine were heated together at 100° C. for 20 hrs. From the reaction mixture there was isolated an 80% yield of 2,5-dimethyl-6-piperidinohex-4-en-2-ol.

Sources & evidence

ORD record
ord-36b3dc7de3a744b7b84c6924ec4ae3cb
Source dataset
uspto-grants-1979_11
Patent number
US04175187

Linked notes

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