Hydrogen Bromide → 1'-Benzyl-3-(4-isopropylphenyl)-4,6,7-trimethylspiro[benzofuran-2(3H), 4'-piperidine]-5-ol

HRID 1743200Notes

Reaction equation

HRID 1743200 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:25]2[C:30]([CH3:31])=[C:29]([O:32]C)[C:28]([CH3:34])=[C:27]([CH3:35])[C:26]=2[O:36]C)([C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=2)O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.[OH-].[Na+]>C(O)(=O)C>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]2([CH:14]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=3)[C:25]3[C:30]([CH3:31])=[C:29]([OH:32])[C:28]([CH3:34])=[C:27]([CH3:35])[C:26]=3[O:36]2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 22238283(1-Benzyl-4-piperidyl)(2,5-dimethoxy-3,4,6-trimethylphenyl)(4-isopropylphenyl)methanol

Product 1

HCID 222382651'-Benzyl-3-(4-isopropylphenyl)-4,6,7-trimethylspiro[benzofuran-2(3H), 4'-piperidine]-5-olYield 76.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of (1-benzyl-4-piperidyl)(2,5-dimethoxy-3,4,6-trimethylphenyl)(4-isopropylphenyl)methanol (6.41 g, 12.8 mmol) in acetic acid (50 mL) was added 48% hydrobromic acid (60 mL), and the mixture was heated under reflux for 15 hours in an argon atmosphere. The reaction mixture was cooled to room temperature, made basic with 8N sodium hydroxide solution, and extracted twice with ethyl acetate. The organic layers were combined, washed with an aqueous saturated sodium hydrogencarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to obtain the title compound (4.44 g, yield 76%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hours in an argon atmosphere
  3. extractionextracted twice with ethyl acetate
  4. washwashed with an aqueous saturated sodium hydrogencarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-23241456813b48079441bef9b70dbd10
Source dataset
uspto-grants-2006_03
Patent number
US07008950B1

Reaction notes

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