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

HRID 1912063Notes

Reaction equation

HRID 1912063 reaction equation
[CH3:1][C:2]([CH3:14])([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][C:2]([CH3:14])([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 539883484,4-Dimethyl-1-piperidin-1-ylpentan-1-one

Product 1

HCID 866750371-(4,4-Dimethyl-1-pentenyl)piperidineYield 250.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4,4-Dimethyl-1-piperidin-1-ylpentan-1-one (508 g) and toluene (1220 mL) were mixed. After an addition of (Ph3P)IrCl(CO) (802 mg) to the mixture, 1,1,3,3-tetramethyldisiloxane (795 mL) was added dropwise to the reaction under water-cooling. The mixture was stirred at RT for 3 hr, then concentrated in vacuo to give the title compound (1171 g) as a crude product.

Workup

  1. additionwas added dropwise to the reaction under water-
  2. temperaturecooling
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40e7d28d4897458dab1ab4ee911297f8
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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