2,2,6,6-Tetramethylpiperidine → HCID 178418821, compound

HRID 1089916Notes

Reaction equation

HRID 1089916 reaction equation
C([Li:5])CCC.[CH3:6][C:7]1([CH3:15])[CH2:12][CH2:11][CH2:10][C:9]([CH3:14])([CH3:13])[NH:8]1.C1(S(N2C3C(=CN=CC=3)C=C2)(=O)=O)C=CC=CC=1.C1(S(N2C3C(=CN=CC=3)C=C2[Li])(=O)=O)C=CC=CC=1>O1CCCC1.[Mn](Cl)(Cl)=O>[Li:5][N:8]1[C:9]([CH3:14])([CH3:13])[CH2:10][CH2:11][CH2:12][C:7]1([CH3:15])[CH3:6]

Participants

7

Reactant 4

HCID 130352,2,6,6-TetramethylpiperidineHCID 110106571-(Phenylsulfonyl)-1H-pyrrolo[3,2-c]pyridineHCID 178418339ButyllithiumHCID 178506647HCID 178506647, compound

Product 1

HCID 178418821HCID 178418821, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178526220HCID 178526220, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of 0.15 mole of lithium 2,2,6,6-tetramethylpiperidide is prepared by the addition of 0.15 mole of n-butyllithium to 0.15 mole of 2,2,6,6-tetramethylpiperidine in 120 ml of tetrahydrofuran at a temperature lower than -20° C. This solution is then added over a period of a few minutes to 0.1 mole of 1-benzenesulfonyl 5-aza indole cooled to -70° C. while maintaining this temperature throughout the addition. 0.15 mole of anhydrous manganous chloride is then added to the solution of 1-benzenesulfonyl 2-lithio 5-aza indole. The temperature of the medium is then brought from -65° C. to -25° C. in order to bring the exchange reaction to completion and obtain a solution of the desired manganous derivative which is used as such.

Workup

  1. temperaturewhile maintaining this temperature
  2. additionthroughout the addition
  3. customis then brought from -65° C. to -25° C. in order
  4. customthe exchange reaction to completion
  5. customobtain a solution of the desired manganous derivative which

Sources & evidence

ORD record
ord-7c20623e91274cff997eeb6cac14a0f0
Source dataset
uspto-grants-1992_01
Patent number
US05079363

Reaction notes

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