Chlorotrimethylsilane → HCID 54514362, compound

HRID 2400030Notes

Reaction equation

HRID 2400030 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH3:14][Si:15](Cl)([CH3:17])[CH3:16]>C1COCC1>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:13]=[CH:12][C:10]([N:11]([Si:15]([CH3:17])([CH3:16])[CH3:14])[Si:15]([CH3:17])([CH3:16])[CH3:14])=[CH:9][CH:8]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 75655Benzenamine, 4-(4-morpholinyl)-

Product 1

HCID 54514362HCID 54514362, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Morpholinoaniline (1 g, 5.61 mmol) was dissolved in dry THF (25 ml). N-BuLi (1.41M, 8.8 ml) was added dropwise at 0° C. over 5 minutes and the solution changed from brown to yellow. After stirring for 2.5 hours while warming to room temperature, trimethylsilyl chloride (97%, 1.62 ml) was added, followed by stirring at room temperature for 12 hours. Evaporation of the solvent gave a yellow solid which was sublimed at 10-4 torr to produce pure 4-morpholino-N,N-bistrimethylsilyl aniline as white solid (1.32 g, 73%). 1H NMR (CDCl3) 6.75 (s, Ph, 4H), 3.81 (t, CH2, 4H), 3.05 (t, CH2, 4H), 0.03 (s, TMS, 18H) .

Workup

  1. stirringby stirring at room temperature for 12 hours
  2. customEvaporation of the solvent
  3. customgave a yellow solid which

Sources & evidence

ORD record
ord-95708120107c47b9b015ff2cfc3dcf7e
Source dataset
uspto-grants-1995_09
Patent number
US05453220

Reaction notes

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