Chlorotrimethylsilane → ethyl N-trimethylsilylpiperidin-4-ylcarboxylate

HRID 482275Notes

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.[CH3:12][Si:13](Cl)([CH3:15])[CH3:14]>>[CH3:12][Si:13]([CH3:15])([CH3:14])[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

Reactant 2

HCID 6397Chlorotrimethylsilane

HCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 22006945ethyl N-trimethylsilylpiperidin-4-ylcarboxylate

Procedure

In an alternative method, ethyl piperidin-4-ylcarboxylate was reacted with trimethylsilyl chloride, yielding ethyl N-trimethylsilylpiperidin-4-ylcarboxylate (B). Intermediate (B) was then reacted with a two to three molar excess of the Grignard reagent of an appropriately substituted halide, as described above, affording a 4-[bis(substituted)hydroxymethyl]piperidine (C), for example 4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine. Intermediate (C) was reacted with an appropriately substituted phenylalkyl halide, as described above, yielding the corresponding intermediate N-(substituted alkyl)-4-[bis(substituted)hydroxymethyl]piperidine (I). The N-oxide of (I) and the targeted salts and betaines were prepared as describes above.

Sources & evidence

ORD record: ord-13770b17b24d46a8bf91ef8eed08494d
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05795901

Reaction notes

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