Piperidin-4-ol → HCID 58072141, compound

HRID 870476Notes

Reaction equation

HRID 870476 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[C:8]([Si:12](Cl)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:11])([CH3:10])[CH3:9]>O1CCCC1>[Si:12]([O:7][CH:4]1[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]1)([C:8]([CH3:11])([CH3:10])[CH3:9])([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 58072141HCID 58072141, compoundYield 8.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 250-mL round-bottom flask was placed a solution of piperidin-4-ol (4 g, 39.55 mmol, 1.00 equiv) in tetrahydrofuran (100 mL), TEA (12 g, 118.59 mmol, 3.00 equiv) and tert-butyl(chloro)diphenylsilane (16 g, 58.21 mmol, 1.47 equiv). The resulting solution was stirred for 16 h at room temperature. The solids were filtered out. The filtrate was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:2). Purification afforded 1.1 g (8%) of 4-[(tert-butyldiphenylsilyl)oxy]piperidine as a colorless oil.

Workup

  1. customInto a 250-mL round-bottom flask was placed
  2. filtrationThe solids were filtered out
  3. dry with materialThe filtrate was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customPurification

Sources & evidence

ORD record
ord-bb0964ffce9f4900a4c4c9e62499dd59
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Reaction notes

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