3-Methoxyaniline → HCID 43121631, compound

HRID 349213Notes

Reaction equation

HRID 349213 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=O)[CH2:2]2.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[CH:13]=1.[BH4-].[Na+]>CCO>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([NH:18][CH:3]2[CH:4]3[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]3)[CH2:2]2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 108243-MethoxyanilineHCID 195073-QuinuclidinoneHCID 4311764Sodium borohydride

Product 1

HCID 43121631HCID 43121631, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

(Method 2A) A solution of 1-azabicyclo[2.2.2]octan-3-one (8.1 g, 50 mmol), m-anisidine (6.2 g, 50.0 mmol) and 4Å molecular sieves in 50 mL of EtOH was stirred at room temperature overnight. NaBH4 pellets were added until the reaction was judged complete by TLC, at which point most of the EtOH was evaporated in vacuo and the residue was partitioned between 3N NaOH and EtOAc. The aqueous layer was extracted with a second portion of EtOAc. The organic layers were combined and washed with water and then brine and then dried over NaSO4. The solution was filtered and the solvent was evaporated in vacuo. The residue was dissolved in 2-PrOH and treated with 1.5 g of fumaric acid. The product was collected and recrystallized from 2-PrOH to give N-(3-methoxyphenyl)-1-azabicyclo[2.2.2]octan-3-amine (5.2 g, 30%) as an intermediate, an off-white solid. MH+=233.

Workup

  1. customwas evaporated in vacuo
  2. customthe residue was partitioned between 3N NaOH and EtOAc
  3. extractionThe aqueous layer was extracted with a second portion of EtOAc
  4. washwashed with water
  5. dry with materialbrine and then dried over NaSO4
  6. filtrationThe solution was filtered
  7. customthe solvent was evaporated in vacuo
  8. dissolutionThe residue was dissolved in 2-PrOH
  9. additiontreated with 1.5 g of fumaric acid
  10. customThe product was collected
  11. customrecrystallized from 2-PrOH

Sources & evidence

ORD record
ord-35ca7c13e23f47f789fc767804351408
Source dataset
uspto-grants-2007_02
Patent number
US07179818B2

Reaction notes

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