2,2,6,6-Tetramethylpiperidine → HCID 13339631, compound

HRID 1632127Notes

Reaction equation

HRID 1632127 reaction equation
CC1(C)CCCC(C)(C)N1.C([Li])CCC.Br[C:17]([C:24]1[CH:29]=[C:28]([Cl:30])[N:27]=[C:26]([Cl:31])[CH:25]=1)([CH3:23])[CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20]>CCCCCC.O1CCCC1>[Cl:31][C:26]1[CH:25]=[C:24]([C:17](=[CH2:23])[CH2:18][C:19]([Cl:20])([Cl:21])[Cl:22])[CH:29]=[C:28]([Cl:30])[N:27]=1

Participants

6

Reactant 3

HCID 130352,2,6,6-TetramethylpiperidineHCID 13339641HCID 13339641, compoundHCID 178418339Butyllithium

Product 1

HCID 13339631HCID 13339631, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-75 °C

Procedure

To a dried tetrahydrofuran solution of 4.03 g of 2,2,6,6-tetramethylpiperidine under N2 was added 17.8 ml of 1.6M n-butyllithium in hexane. The solution was cooled to -75° C. and a concentrated solution of 4-(1-bromo-3,3,3-trichloro-1-methylpropyl)-2,6-dichloropyridine in tetrahydrofuran was added to maintain ≤-65° C. The mixture was stirred at -65° C. for two hours and quenched with 20 mls of water. The organics were extracted with ether, dried (MgSO4), and concentrated in vacuo. The crude product was purified via high pressure liquid chromatography, yielding 5 g (68%), m.p. 66°-67.5° C.

Workup

  1. temperatureto maintain ≤-65° C
  2. customquenched with 20 mls of water
  3. extractionThe organics were extracted with ether
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified via high pressure liquid chromatography
  7. customyielding 5 g (68%), m.p. 66°-67.5° C.

Sources & evidence

ORD record
ord-3d3fd72dc3d74a54b6679bdce26c4011
Source dataset
uspto-grants-1984_10
Patent number
US04474602

Reaction notes

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