Chlorotrimethylsilane → ethyl N-trimethylsilylpiperidin-4-ylcarboxylate

HRID 634853Notes

Reaction equation

HRID 634853 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.Cl[Si:20]([CH3:23])([CH3:22])[CH3:21]>C(OCC)C>[CH3:21][Si:20]([CH3:23])([CH3:22])[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 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under a nitrogen atmosphere, a stirred solution of 100.0 grams (0.64 mole) of ethyl piperidin-4-ylcarboxylate and 94 mL (0.67 mole) of triethylamine in 1400 mL of diethyl ether was cooled to 15° C., and a solution of 86 mL (0.68 mole) of chlorotrimethylsilane in 100 mL of diethyl ether was added dropwise during a 30 minute period. Upon completion of the addition, the thick reaction mixture was stirred vigorously for one hour while warming to ambient temperature. The reaction mixture was then filtered, and the collected solid was washed with diethyl ether. The combined wash and filtrate were concentrated under reduced pressure to a residual oil. The oil was distilled under reduced pressure, yielding 115.0 grams (79% yield) of ethyl N-(trimethylsilyl)piperidin-4-ylcarboxylate, bp 75° C./0.1 mm Hg. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition
  2. filtrationThe reaction mixture was then filtered
  3. washthe collected solid was washed with diethyl ether
  4. washThe combined wash
  5. concentrationfiltrate were concentrated under reduced pressure to a residual oil
  6. distillationThe oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-7da67381cc7b4c3f98f5c17c0e82f623
Source dataset
uspto-grants-2001_02
Patent number
US06184234B2

Reaction notes

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