Benzene → HCID 54406719, compound

HRID 1605816Notes

Reaction equation

HRID 1605816 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].C1C=CC=CC=1.[CH:11]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:13]([NH:14][CH2:15]3)[CH2:12]1)[CH2:19]2.C(OC(=O)C)(=O)C>C(O)(=O)C>[CH2:1]([N:14]1[CH2:15][CH:16]2[CH2:21][CH:11]3[CH2:19][CH:18]([CH2:20][CH:13]1[CH2:12]3)[CH2:17]2)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 241Benzene2×HCID 7841Allyl bromideHCID 7918Acetic AnhydrideHCID 322724-Azatricyclo[4.3.1.13,8]undecane

Product 1

HCID 54406719HCID 54406719, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a well stirred solution of 1.2 gm. (0.01 mole) of allyl bromide in 50 ml. of benzene, a solution of 1.5 gm. (0.01 mole) of 4-azatricyclo[4.3.1.13,8 ]undecane in 50 ml. of benzene is added dropwise. The mixture is refluxed 1 hr., cooled, and 1 gm. of acetic anhydride is added. The mixture is refluxed an additional 2 hrs., cooled, poured into ice water and acidified with acetic acid. The layers are separated and the aqueous layer is extracted with ether. The acidic aqueous layer is made basic with NaOH, and extracted with chloroform. The chloroform extract is washed with water, dried over magnesium sulfate, filtered and the solvent evaporated to give 4-allyl- 4-azatricyclo[4.3.1.13,8 ]undecane.

Workup

  1. temperatureThe mixture is refluxed 1 hr
  2. temperature, cooled
  3. temperatureThe mixture is refluxed an additional 2 hrs
  4. temperature, cooled
  5. customThe layers are separated
  6. extractionthe aqueous layer is extracted with ether
  7. extractionextracted with chloroform
  8. extractionThe chloroform extract
  9. washis washed with water
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customthe solvent evaporated

Sources & evidence

ORD record
ord-13e899b9d29b4fcda7aa5ce96f27d12e
Source dataset
uspto-grants-1976_04
Patent number
US03951950

Reaction notes

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