3-Bromotoluene → 1-Benzyl-4-(3-methylphenyl)-4-piperidinol

HRID 2111604Notes

Reaction equation

HRID 2111604 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[CH:4]=1.[CH2:10]([N:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH2:10]([N:17]1[CH2:22][CH2:21][C:20]([C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[CH:4]=2)([OH:23])[CH2:19][CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 115603-BromotolueneHCID 192201-Benzyl-4-piperidoneHCID 5462224Magnesium

Product 1

HCID 179670241-Benzyl-4-(3-methylphenyl)-4-piperidinolYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

This compound is prepared according to the procedure described in step A of Preparation 8.3, starting with 3.4 g of magnesium in 15 ml of THF, a solution of 20 g of 1-bromo-3-methylbenzene in 100 ml of THF and a solution of 22.13 g of 1-benzyl-4-piperidone in 100 ml of THF. 26.54 g of the expected product are obtained.

Workup

  1. customThis compound is prepared
  2. customdescribed in step A of Preparation 8.3

Sources & evidence

ORD record
ord-3d6782490e4b4da09495940d4f7aafe8
Source dataset
uspto-grants-2009_04
Patent number
US07521449B2

Reaction notes

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