Water → HCID 10039345, compound

HRID 1197542Notes

Reaction equation

HRID 1197542 reaction equation
[C:1]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1CCOCC1.[Br:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Br.O>C1(C)C=CC=CC=1.O1CCOCC1.CC1C=CC(S(O)(=O)=O)=CC=1>[Br:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:1]1=[O:8]

Participants

8

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 10400CycloheptanoneHCID 769652-Bromobenzyl bromide

Product 1

HCID 10039345HCID 10039345, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of cycloheptanone (56.1 g, 0.5 mol) in toluene (500 ml) was added morpholine (65.3 g, 0.75 mol) and tosic acid (100 mg). The reaction vessel was fitted with a Dean-Stark condenser and the reaction was refluxed for 24 hours. The toluene was removed in vacuo and the enamine was vacuum distilled. The enamine was collected as a pale yellow oil (46.5 g, 51%). To a solution of the enamine (10.0 g, 0.055 mol) in dioxane (50 ml) was added 2-bromobenzyl bromide and the reaction was refluxed overnight. Water (10 ml) was then added and the mixture was refluxed an additional 2 hours. The reaction was cooled and the solvent was removed in vacuo. The residue was partitioned between dichloromethane and 1N hydrochloric acid. The dichloromethane layer was washed with additional 1N hydrochloric acid (50 ml) and water (50 ml), dried (MgSO4), filtered, and reduced in volume to yield a crude orange oil (15.9 g). The mixture was vacuum distilled to yield the title compound as a clear oil (8.5 g, 55%) that was a semisolid at 23° C.

Workup

  1. customThe reaction vessel was fitted with a Dean-Stark condenser
  2. temperaturethe reaction was refluxed for 24 hours
  3. customThe toluene was removed in vacuo
  4. distillationdistilled
  5. customThe enamine was collected as a pale yellow oil (46.5 g, 51%)
  6. temperaturethe reaction was refluxed overnight
  7. temperaturethe mixture was refluxed an additional 2 hours
  8. temperatureThe reaction was cooled
  9. customthe solvent was removed in vacuo
  10. customThe residue was partitioned between dichloromethane and 1N hydrochloric acid
  11. washThe dichloromethane layer was washed with additional 1N hydrochloric acid (50 ml) and water (50 ml)
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered
  14. customto yield a crude orange oil (15.9 g)
  15. distillationdistilled

Sources & evidence

ORD record
ord-07e8eaf32fbd4b7d9b8645fffcbd7f5b
Source dataset
uspto-grants-1994_01
Patent number
US05276053

Reaction notes

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