Chlorotrimethylsilane → ethyl N-trimethylsilylpiperidin-4-ylcarboxylate

HRID 482278Notes

Reaction equation

HRID 482278 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:19][Si:20](Cl)([CH3:22])[CH3:21]>C(OCC)C>[CH3:19][Si:20]([CH3:22])([CH3:21])[N:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 22006945ethyl N-trimethylsilylpiperidin-4-ylcarboxylateYield 93.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under a nitrogen atmosphere a stirred solution of 50.0 grams (0.313 mole) of ethyl piperidin-4-ylcarboxylate in 300 mL of diethyl ether was cooled to 0° C. and 33.8 grams (0.338 mole) of triethylamine was added in one portion. To this was added dropwise during a 30 minute period a solution of 34.6 grams (0.338 mole) of trimethylsilyl chloride in 100 mL of diethyl ether. Upon completion of the addition the reaction mixture was stirred for five hours, then it was filtered to remove triethylamine hydrochloride. The filtrate was concentrated under reduced pressure to a residue. The residue was then dissolved in 200 mL of hexane in which it was allowed to stand for about two hours under a nitrogen atmosphere. The solution was filtered and concentrated under reduced pressure, yielding 66.9 grams of ethyl N-trimethylsilylpiperidin-4-ylcarboxylate. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. filtrationit was filtered
  3. customto remove triethylamine hydrochloride
  4. concentrationThe filtrate was concentrated under reduced pressure to a residue
  5. dissolutionThe residue was then dissolved in 200 mL of hexane in which it
  6. waitto stand for about two hours under a nitrogen atmosphere
  7. filtrationThe solution was filtered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9427611f217e44e88ca74ede34584499
Source dataset
uspto-grants-1998_08
Patent number
US05795901

Reaction notes

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