Lithium Hexamethyldisilazide → HCID 59299455, compound

HRID 2235311Notes

Reaction equation

HRID 2235311 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[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][C:27]=1[Cl:33]>CN(C=O)C>[Br:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][CH:9]2[CH2:10][CH2:11][CH2:12][N:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:8]2=[O:13])=[C:27]([Cl:33])[CH:28]=1

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 14178413HCID 14178413, compoundHCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzene

Product 1

HCID 59299455HCID 59299455, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve 1-cyclohexyl-piperidin-2-one (0.2 g, 1.10 mmol) in dry DMF (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-4-bromobenzene (0.63 g, 2.21 mmol), and allow the mixture to warm to room temperature over 15 h. Partition the mixture between ether and 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 (0.16 g, 38%). MS (ES+) m/z=384, 386 (M+H)+.

Workup

  1. temperatureto warm to room temperature over 15 h
  2. customPartition the mixture between ether and 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-8bc2cb654de740668735b4f2686bf29c
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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