Tetrahydrofuran → 1-Benzyl-4-methylpiperidin-4-ol

HRID 473799Notes

Reaction equation

HRID 473799 reaction equation
C[Mg]Br.[CH2:4]([N:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O1CCC[CH2:19]1.[Cl-].[NH4+]>C(OCC)C>[CH2:4]([N:11]1[CH2:16][CH2:15][C:14]([CH3:19])([OH:17])[CH2:13][CH2:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 192201-Benzyl-4-piperidoneHCID 25517Ammonium ChlorideHCID 178418573HCID 178418573, compound

Product 1

HCID 108459131-Benzyl-4-methylpiperidin-4-olYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl magnesium bromide (6.00 mmol) in ethyl ether (27 mL) was added 1-benzyl-piperidin-4-one (0.53 g, 0.28 mmol) at 0° C. followed by tetrahydrofuran (10 mL). The reaction mixture was warmed to room temperature and stirred for 18 h. Saturated ammonium chloride was added and the aqueous layer was extracted with ethyl acetate (3×). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Column chromatography on silica (2-10% methanol in dichloromethane) afforded 1-benzyl-4-methylpiperidin-4-ol (0.42 g, 72% yield).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d2c4bc42cfec42618f5d857c0fbd1e9e
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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