Ethylene Glycol → 8-(4-Nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 1910778Notes

Reaction equation

HRID 1910778 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:17](O)[CH2:18][OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][C:13]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:14][CH2:15]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 38425621-(4-Nitrophenyl)piperidin-4-one

Product 1

HCID 71470798-(4-Nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decaneYield 67.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(4-nitrophenyl)-4-piperidone (0.6 g, 2.7 mmol), ethylene glycol (0.3 mL, 5.4 mmol) and p-toluenesulfonic acid (0.1 g in toluene (20 mL) was heated at reflux in a Dean-Stark apparatus until no more water accumulation occurred. The reaction was evaporated to dryness and the residue partitioned between ethyl acetate and water. The organic layer was separated and washed with water then brine and dried over sodium sulfate. Concentration under reduced pressure afforded 8-(4-nitrophenyl)-1,4-dioxa-8-aza-spiro[4,5]decane (0.48 g, 66%).

Workup

  1. temperaturewas heated
  2. customThe reaction was evaporated to dryness
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialbrine and dried over sodium sulfate
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-316ade668c014bb5bd6a6e14b662ecbf
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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