1-Benzyl-4-piperidone → 1-Benzyl-4-methylpiperidin-4-ol

HRID 456741Notes

Reaction equation

HRID 456741 reaction equation
[CH3:1][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>O1CCCC1>[CH2:4]([N:11]1[CH2:16][CH2:15][C:14]([CH3:1])([OH:17])[CH2:13][CH2:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 192201-Benzyl-4-piperidoneHCID 178418573HCID 178418573, compound

Product 1

HCID 108459131-Benzyl-4-methylpiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under nitrogen atmosphere, methylmagnesium bromide (3.0M solution in diethyl ether, 10.8 mL) was diluted with tetrahydrofuran (110 mL) with cooling on an ice bath. To the solution, was added dropwise a solution of 1-benzyl-4-piperidinone (5.6 g) in tetrahydrofuran (40 mL), and the mixture was stirred for 1 hr.

Workup

  1. temperaturewith cooling on an ice bath

Sources & evidence

ORD record
ord-7b5e29e25b744775b2131ce49df9c7c5
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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