Chlorotrimethylsilane → HCID 63911765, compound

HRID 336128Notes

Reaction equation

HRID 336128 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH:4]([CH3:8])[NH:3]1.[Li]CCCC.C[Si](Cl)(C)C.[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20]>C1COCC1>[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([N:3]2[CH:4]([CH3:8])[CH2:5][NH:6][CH2:7][CH:2]2[CH3:1])=[O:27])=[CH:29][CH:30]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 85024-Nitrobenzoyl chlorideHCID 660562,6-DimethylpiperazineHCID 178418339Butyllithium

Product 1

HCID 63911765HCID 63911765, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2,6-di-methylpiperazine (LV, 5.0 g, 43.8 mmol) in dry THF (50 mL), maintained at room temperature under an argon atmosphere, was added a solution of 2.5 M n-BuLi in THF (38.54 mL, 96.36 mmol). After the mixture was stirred for 30 min at room temperature, trimethylsilyl chloride (5.5 mL, 43.8 mmol) was added and the reaction mixture stirred for 1 h before the addition of 4-nitrobenzoyl chloride (7.8 gm, 42.05 mmol). After 10 min, the reaction mixture was quenched with MeOH and the solvents were evaporated in vacuo. The residue was purified by silica gel column chromatography to provide product LVI (10.37 gm, 90% yield):

Workup

  1. waitAfter 10 min
  2. customthe reaction mixture was quenched with MeOH
  3. customthe solvents were evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. customto provide product LVI (10.37 gm, 90% yield)

Sources & evidence

ORD record
ord-e1beb29b379a4fedbd66379b565e3f7c
Source dataset
uspto-grants-2014_11
Patent number
US08889667B2

Reaction notes

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