Hydrogen Bromide → HCID 22238258, compound

HRID 1743204Notes

Reaction equation

HRID 1743204 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:16]2[C:21]([CH3:22])=[C:20]([O:23]C)[C:19]([CH3:25])=[C:18]([CH3:26])[C:17]=2[O:27]C)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[CH2:13][CH2:12][C:11]2([CH2:14][C:16]3[C:21]([CH3:22])=[C:20]([OH:23])[C:19]([CH3:25])=[C:18]([CH3:26])[C:17]=3[O:27]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 22238270HCID 22238270, compound

Product 1

HCID 22238258HCID 22238258, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of (1-benzyl-4-piperidyl)(2,5-dimethoxy-3,4,6-trimethylphenyl)methanol (6.10 g, 15.9 mmol) in acetic acid (30 mL) was added 48% hydrobromic acid (40 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 subjected to silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain the title compound (4.60 g, yield 86%). This was amorphous.

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

Sources & evidence

ORD record
ord-aadcfcbbe18e4dcbaaae79c3560327aa
Source dataset
uspto-grants-2006_03
Patent number
US07008950B1

Reaction notes

Loading…