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

HRID 2376643Notes

Reaction equation

HRID 2376643 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]([CH3:9])[CH:6]=[CH:7][CH:8]=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-piperidinol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

This compound is prepared by the procedure described in step A of preparation 1.7, from 1.55 g of magnesium in 25 ml of THF, a solution of 11 g of 3-bromotoluene in 15 ml of THF and a solution of 10 g of 1-benzyl-4-piperidone in 30 ml of THF. The product obtained is chromatographed on silica gel, eluting with a DCM/MeOH (97/3; v/v) mixture. This gives 14.5 g of the expected product.

Workup

  1. customThis compound is prepared by the procedure
  2. customThe product obtained
  3. customis chromatographed on silica gel
  4. washeluting with a DCM/MeOH (97/3; v/v) mixture

Sources & evidence

ORD record
ord-c617128cc4974fc5ad39c9da4ebb9694
Source dataset
uspto-grants-2008_12
Patent number
US07468368B2

Reaction notes

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