Piperidine → 2,6-Dimethyl-6-piperidino-4-hepten-2-ol

HRID 46803

Reaction equation

HRID 46803 reaction equation
[CH3:1][C:2]([CH3:5])=[CH:3]Br.[CH3:6][C:7]([OH:11])([CH:9]=[CH2:10])[CH3:8].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]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>[CH3:6][C:7]([OH:11])([CH2:9][CH:10]=[CH:1][C:2]([CH3:5])([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH3:3])[CH3:8]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 82572-Methyl-3-buten-2-olHCID 11776TriphenylphosphineHCID 985601-Bromo-2-methyl-1-propene

Product 1

HCID 540231822,6-Dimethyl-6-piperidino-4-hepten-2-olYield 31%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A mixture of 10 mmoles 2-methyl-1-bromo-1-propene, 12.5 mmoles 2-methyl-3-buten-2-ol, 30 mmoles piperidine, 0.20 mmole palladium acetate and 0.40 mmole triphenylphosphine was reacted at 100° C. There was produced 61% of a mixture of nonadienols, 31% 2,6-dimethyl-6-piperidino-4-hepten-2-ol and 6% of what is believed to be 2,6-dimethyl-4-piperidino-5-hepten-2-ol.

Workup

  1. customwas reacted at 100° C

Sources & evidence

ORD record
ord-2a8da2881cb74fe29c07cbad6f53654a
Source dataset
uspto-grants-1979_11
Patent number
US04175187

Linked notes

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