Triethylamine → 2-[(3-Azabicyclo[3.2.2]non-3-yl)acetyl]-6-methylaniline

HRID 1596361Notes

Reaction equation

HRID 1596361 reaction equation
[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][NH:3][CH2:2]2.[CH2:10](N(CC)CC)C.ClCC([NH:21][C:22]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24]C=1)=O.C([O:32][CH2:33][CH3:34])(=O)C>C(Cl)Cl.CCCCCC.C(OC(C)C)(C)C>[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([CH2:10][C:33]([C:34]1[CH:24]=[CH:25][CH:26]=[C:27]([CH3:28])[C:22]=1[NH2:21])=[O:32])[CH2:2]2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 92403-Azabicyclo[3.2.2]nonaneHCID 101479Acetamide, 2-chloro-N-(2-methylphenyl)-

Product 1

HCID 217013412-[(3-Azabicyclo[3.2.2]non-3-yl)acetyl]-6-methylanilineYield 88.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 7914Diisopropyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a solution of 3-azabicyclo[3.2.2]nonane (1.1 g) and triethylamine (0.88 g) in methylene chloride (25 ml) was added portionwise 2-chloroacetyl-6-methylaniline (1.47 g) under stirring and cooling in an ice-bath. After the addition was completed, the mixture was stirred at ambient temperature overnight. Removal of the solvent afforded a residue, which was dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo to give a crystalline mass, which was pulverized in a mixture of n-hexane and diisopropyl ether. A dark yellow crystal was collected by filtration to give 2-[(3-azabicyclo[3.2.2]non-3-yl)acetyl]-6-methylaniline (1.92 g, 88.2%).

Workup

  1. temperaturecooling in an ice-bath
  2. additionAfter the addition
  3. stirringthe mixture was stirred at ambient temperature overnight
  4. customRemoval of the solvent
  5. customafforded a residue, which
  6. washwashed with water and brine
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customevaporated in vacuo
  9. customto give a crystalline mass, which
  10. filtrationA dark yellow crystal was collected by filtration

Sources & evidence

ORD record
ord-d14438e7f5244894a3610c910765a481
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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