Lithium Hexamethyldisilazide → HCID 59299368, compound

HRID 2235310Notes

Reaction equation

HRID 2235310 reaction equation
[CH:1]1([N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:25][C:26]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:33]>C1COCC1>[Cl:33][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([F:32])[C:26]=1[CH2:25][CH:9]1[CH2:10][CH2:11][CH2:12][N:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:8]1=[O:13]

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 27736252-Chloro-6-fluorobenzyl bromideHCID 14178413HCID 14178413, compound

Product 1

HCID 59299368HCID 59299368, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve 1-cyclohexyl-piperidin-2-one (0.2 g, 1.10 mmol) in dry THF (11 mL) cool to −78° C. and add lithium bis(trimethylsilyl)amide (1.66 mL of 1.0 M solution in THF, 1.66 mmol). After 15 min add 1-bromomethyl-2-chloro-6-fluorobenzene (0.49 g, 2.21 mmol), and allow the mixture to warm to room temperature over 15 h. Wash the mixture with brine, dry the organic layer over sodium sulfate and evaporate. Purify the residue by chromatography on silica gel (eluting 0% to 100% ethyl acetate in hexane) to give the desired product (0.21 g, 59%). MS (ES+) m/z=324 (M+H)+.

Workup

  1. temperatureto warm to room temperature over 15 h
  2. washWash the mixture with brine
  3. dry with materialdry the organic layer over sodium sulfate
  4. customevaporate
  5. customPurify the residue by chromatography on silica gel (eluting 0% to 100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-85d18fd803324c979b7b5bdb07d2b1b4
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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