1-Bromododecane → 1-Dodecylazacyclohept-4-ene-2-one

HRID 845106Notes

Reaction equation

HRID 845106 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3][C:2]1=[O:8].N1CCC=CCC1=O.[H-].[Na+].[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C1COCC1.O>[CH2:30]([N:1]1[CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][C:2]1=[O:8])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19]

Participants

7

Reactant 4

HCID 89191-BromododecaneHCID 24758Sodium hydrideHCID 5575022,5,6,7-tetrahydro-1H-azepin-2-oneHCID 123480732,3,6,7-tetrahydro-1H-azepin-2-one

Product 1

HCID 141826971-Dodecylazacyclohept-4-ene-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 11.4 g (0.102 mol) of a mixture of azacyclohept-3-ene-2-one and azacyclohept-4-ene-2-one (Example 3-C) in THF was added dropwise to a suspension of 4.8 g (107 mmol) of sodium hydride (50% oil dispersion) in THF. The mixture was stirred at room temperature for 1 hour, 25.4 g (0.102 mol) of dodecyl bromide was added, and the solution was refluxed for 5 hours. The mixture was cooled, water was added, and the solvent was removed in vacuo. The residue was dissolved in CH2Cl2, washed with water, the organic phase dried over MgSO4 and concentrated in vacuo to yield an oil which was Kugelrohr distilled to give 15.5 g of a crude product. This material was subjected to flash chromatography (silica gel; 9:1 petroleum ether/ether V/V) to give 1-dodecylazacyclohept-4-ene-2-one, Rf =0.45; GC retention time 7.4 min. GC conditions identical to Example 3-D.

Workup

  1. temperaturethe solution was refluxed for 5 hours
  2. temperatureThe mixture was cooled
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. washwashed with water
  6. dry with materialthe organic phase dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto yield an oil which
  9. distillationdistilled
  10. customto give 15.5 g of a crude product

Sources & evidence

ORD record
ord-ac13d4a489424fd99b85fe6254712b3d
Source dataset
uspto-grants-1988_07
Patent number
US04755535

Reaction notes

Loading…