2,2,5,5-Tetramethylpyrrolidine → HCID 22750211, compound

HRID 2164078Notes

Reaction equation

HRID 2164078 reaction equation
[O:1]1[CH2:19][CH:2]1[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:18])[C:9]=2[CH:8]=[CH:7][CH:6]=1.[CH3:20][C:21]1([CH3:28])[CH2:25][CH2:24][C:23]([CH3:27])([CH3:26])[NH:22]1>O1CCOCC1>[OH:1][CH:2]([CH2:19][N:22]1[C:23]([CH3:27])([CH3:26])[CH2:24][CH2:25][C:21]1([CH3:28])[CH3:20])[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:18])[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 783202,2,5,5-TetramethylpyrrolidineHCID 18678486HCID 18678486, compound

Product 1

HCID 22750211HCID 22750211, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4 g of 4-(2,3-epoxypropoxy)-9-fluorenone are heated to 150° in an autoclave for 15 hours together with 4 g of 2,2,5,5-tetramethylpyrrolidine in 30 cc of dioxane. After cooling, the reaction mixture is concentrated by evaporation. The residue is taken up in ether and extracted with 2 N hydrochloric acid. The aqueous solution is made alkaline and thoroughly extracted with methylene chloride. The methylene chloride phase is concentrated by evaporation and the residue is crystallized from ethyl acetate/petroleum ether. The title compound has an M.P. of 137°-139°.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated by evaporation
  3. extractionextracted with 2 N hydrochloric acid
  4. extractionthoroughly extracted with methylene chloride
  5. concentrationThe methylene chloride phase is concentrated by evaporation
  6. customthe residue is crystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-ce516ceaa95f41c39927155ef5d6a5f5
Source dataset
uspto-grants-1979_01
Patent number
US04137331

Reaction notes

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