Dimethylformamide → HCID 86738225, compound

HRID 851049Notes

Reaction equation

HRID 851049 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C@@H:7]2[CH2:12][CH2:11][NH:10][CH2:9][C@H:8]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:21](=[O:24])([O-:23])[O-].[K+].[K+].[CH2:27](Br)[CH:28]=[CH2:29].CN(C)C=[O:34]>>[C:5]([OH:34])(=[O:6])/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:24].[CH2:29]([N:10]1[CH2:11][CH2:12][C@@H:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:20][CH:19]=2)[C@H:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9]1)[CH:28]=[CH2:27]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 12788502HCID 12788502, compound

Product 1

HCID 86738225HCID 86738225, compound

Conditions

Temperature
61 °C

Procedure

A mixture of 4.34 g of trans-4-(4-fluorophenoxy)-3-phenylpiperidine, 4.8 g of anhydrous potassium carbonate, 1.52 ml of allyl bromide and 64 ml of dry dimethylformamide is heated and vigorously stirred overnight at 61° C. under nitrogen. The mixture is cooled to room temperature and partitioned between water (300 ml) and ether (500 ml). The phases are separated and the ether phase is washed with water (3×300 ml), followed by 300 ml of saturated sodium chloride solution. After drying over anhydrous sodium sulfate the ether extracts are filtered and concentrated in vacuo to a light orange oil. The oil is dissolved in ether (100 ml) and treated dropwise with a solution of 1.4 g of fumaric acid in a mixture of ether (125 ml) and ethanol (25 ml). The solvent is removed in vacuo, and the residue triturated with ether containing a small amount of ethanol. Filtration and washing with ether followed by recrystallization from about 100 ml of boiling ethyl acetate with concentration of the filtrate to about 60 ml affords upon cooling and washing with ethyl acetate and ether product as nearly colorless crystals, mp 138°-139.5° C.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. custompartitioned between water (300 ml) and ether (500 ml)
  3. customThe phases are separated
  4. washthe ether phase is washed with water (3×300 ml)
  5. dry with materialAfter drying over anhydrous sodium sulfate the ether extracts
  6. filtrationare filtered
  7. concentrationconcentrated in vacuo to a light orange oil
  8. dissolutionThe oil is dissolved in ether (100 ml)
  9. additiontreated dropwise with a solution of 1.4 g of fumaric acid in a mixture of ether (125 ml) and ethanol (25 ml)
  10. customThe solvent is removed in vacuo
  11. customthe residue triturated with ether containing a small amount of ethanol
  12. filtrationFiltration
  13. washwashing with ether
  14. customfollowed by recrystallization from about 100 ml of boiling ethyl acetate with concentration of the filtrate to about 60 ml
  15. customaffords
  16. temperatureupon cooling
  17. washwashing with ethyl acetate and ether product as nearly colorless crystals, mp 138°-139.5° C.

Sources & evidence

ORD record
ord-d7beb96022f64ddfb0d2a047144954a2
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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