Tetrahydrofuran → 4-Piperidinol, 1-benzyl-4-phenyl-

HRID 1621298Notes

Reaction equation

HRID 1621298 reaction equation
[C:1]1([Mg]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C[O:26]CC1>>[CH2:9]([N:16]1[CH2:21][CH2:20][C:19]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([OH:26])[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 51700761-Benzyl-2-piperidoneHCID 178478979HCID 178478979, compound

Product 1

HCID 973334-Piperidinol, 1-benzyl-4-phenyl-

Procedure

A solution of phenylmagnesium chloride in THF (25%, 33 mL) was added at −10° C. to a solution of 1-Benzylpiperidone (10 g, dissolved in THF). The mixture was warmed to room temperature, stirred for 4 h and quenched by addition of 20% ammonium chloride solution. The mixture was extracted three times with methyl tert. butyl ether and the combined organic layer was dried over sodium sulfate and evaporated to dryness. The crude product was purified by silica gel chromatography to give 14.3 g of the desired product as an orange oil. Rt=1.09 min (Method B). Detected mass: 268.1 (M+H+).

Workup

  1. customquenched by addition of 20% ammonium chloride solution
  2. extractionThe mixture was extracted three times with methyl tert. butyl ether
  3. dry with materialthe combined organic layer was dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-918d55ca90034fb7ae2c47a1d6dc1df0
Source dataset
uspto-grants-2014_07
Patent number
US08772492B2

Reaction notes

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