Hexane → (1-Benzyl-4-piperidyl)(4-isopropylphenyl)(3,4,6-trimethyl-2-methoxyphenyl)methanol

HRID 272354

Reaction equation

HRID 272354 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[CH:6]=[C:5]([CH3:11])[C:4]=1Br.C([Li])CCC.CCCCCC.[CH2:24]([N:31]1[CH2:36][CH2:35][CH:34]([C:37](=[O:47])[C:38]2[CH:43]=[CH:42][C:41]([CH:44]([CH3:46])[CH3:45])=[CH:40][CH:39]=2)[CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1.O>[CH2:24]([N:31]1[CH2:32][CH2:33][CH:34]([C:37]([C:38]2[CH:39]=[CH:40][C:41]([CH:44]([CH3:46])[CH3:45])=[CH:42][CH:43]=2)([C:4]2[C:5]([CH3:11])=[CH:6][C:7]([CH3:10])=[C:8]([CH3:9])[C:3]=2[O:2][CH3:1])[OH:47])[CH2:35][CH2:36]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 219613102-Bromo-3,5,6-trimethylanisoleHCID 219613551-Benzyl-4-(4-isopropylbenzoyl)piperidineHCID 178418339Butyllithium

Product 1

HCID 21961358(1-Benzyl-4-piperidyl)(4-isopropylphenyl)(3,4,6-trimethyl-2-methoxyphenyl)methanolYield 79.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-methoxy-3,4,6-trimethylbromobenzene (15.48 g, 67.56 mmol) in tetrahydrofuran (200 ml), which was kept at −78° C., was added dropwise under an argon atmosphere a solution of n-butyllithium in hexane (1.59 mol/l, 42 ml, 66.78 mmol) and the mixture was stirred for 30 minutes. To this mixture was added dropwise a solution of 1-benzyl-4-(4-isopropylbenzoyl)piperidine (19.81 g, 61.63 mmol) in tetrahydrofuran (50 ml) and the resulting mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture and the product was extracted with ethyl acetate. The extracts were washed with an aqueous saturated solution of sodium chloride, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to obtain 23.01 g (79% yield) of the title compound. Melting point: 154-156° C.

Workup

  1. customwas kept at −78° C.
  2. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  3. extractionthe product was extracted with ethyl acetate
  4. washThe extracts were washed with an aqueous saturated solution of sodium chloride
  5. customdried on magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-090662d5e9834f41b3eccd87ecbc792a
Source dataset
uspto-grants-2008_11
Patent number
US07456162B2

Linked notes

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