1,1,3,3-Tetramethyl-disiloxane → 1-(4-Methyl-1-pentenyl)piperidine

HRID 1912040Notes

Reaction equation

HRID 1912040 reaction equation
[CH3:1][CH:2]([CH3:13])[CH2:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=O.C[SiH](C)O[SiH](C)C>C1(C)C=CC=CC=1>[CH3:1][CH:2]([CH3:13])[CH2:3][CH:4]=[CH:5][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 186591,1,3,3-Tetramethyl-disiloxaneHCID 229808734-Methyl-1-(piperidin-1-YL)pentan-1-one

Product 1

HCID 866750301-(4-Methyl-1-pentenyl)piperidineYield 248.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Methyl-1-piperidin-1-ylpentan-1-one (372.4 g) and toluene (1000 mL) were mixed. To the mixture was added (Ph3P)IrCl(CO) (633 mg). In a water-bath, 1,1,3,3-tetramethyldisiloxane (627 mL) was added dropwise to the mixture. The resulting mixture was stirred at RT for 2 hr. The reaction mixture was concentrated in vacuo to give the title compound (844 g) as a crude product.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-356f1af117b84067a3e5097a7db678d9
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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