Sodium Iodide → Methyl 8-(4-(2-butoxyethoxy)phenyl)-1-(2-methyl-2-propen-1-yl)-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate

HRID 2222832Notes

Reaction equation

HRID 2222832 reaction equation
[OH-].[Na+].[CH2:3]([O:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]3[NH:27][CH2:26][CH2:25][CH2:24][C:23]([C:28]([O:30][CH3:31])=[O:29])=[CH:22][C:21]=3[CH:32]=2)=[CH:13][CH:12]=1)[CH2:4][CH2:5][CH3:6].Br[CH2:34][C:35]([CH3:37])=[CH2:36].[I-].[Na+]>CN(C=O)C.[Cl-].[Na+].O.O>[CH2:3]([O:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:18]=[CH:19][C:20]3[N:27]([CH2:36][C:35]([CH3:37])=[CH2:34])[CH2:26][CH2:25][CH2:24][C:23]([C:28]([O:30][CH3:31])=[O:29])=[CH:22][C:21]=3[CH:32]=2)=[CH:15][CH:16]=1)[CH2:4][CH2:5][CH3:6]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 3577853-Bromo-2-methyl-1-propeneHCID 68650013Methyl 8-(4-(2-butoxyethoxy)phenyl)-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate

Product 1

HCID 68649885Methyl 8-(4-(2-butoxyethoxy)phenyl)-1-(2-methyl-2-propen-1-yl)-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of sodium hydroxide (530 mg) in DMF (10 ml) was added dropwise a solution of methyl 8-(4-(2-butoxyethoxy)phenyl)-1,2,3,4-terahydro-1-benzoazocine-5-carboxylate (1.8 g) in DMF (20 ml) at 0° C. under nitrogen atmosphere. After returning to room temperature and stirring for 1 hour, 3-bromo-2-methylpropene (1.33 ml) and sodium iodide (1.98 g) were added, and the mixture was stirred at 100° C. overnight. After returning to room temperature, water and saturated brine were added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water twice and with saturated brine once, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=12:1→hexane:ethyl acetate=9:1). The resulting residue was recrystallized from hexane-ethyl acetate to give methyl 8-(4-(2-butoxyethoxy)phenyl)-1-(2-methyl-2-propen-1-yl)-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate (1.64 g) as yellow crystals.

Workup

  1. customAfter returning to room temperature
  2. stirringthe mixture was stirred at 100° C. overnight
  3. customAfter returning to room temperature
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water twice
  6. dry with materialwith saturated brine once, and dried with magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=12:1→hexane:ethyl acetate=9:1)
  9. customThe resulting residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-05f52aad3bec4e32864b711453178201
Source dataset
uspto-grants-2008_05
Patent number
US07371772B2

Reaction notes

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