Potassium Carbonate → Trans-1-(4-fluorophenyl)-3-(3-hydroxy-4-phenoxy-1-pyrrolidinyl)-1-propanone

HRID 1381218Notes

Reaction equation

HRID 1381218 reaction equation
[O:1]([CH:8]1[CH2:12][NH:11][CH2:10][CH:9]1[OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)[CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:19](=[O:20])[CH2:18][CH2:17][N:11]2[CH2:12][C@@H:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@H:9]([OH:13])[CH2:10]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123227913-(Dimethylamino)-1-(4-fluorophenyl)propan-1-one hydrochlorideHCID 131922084-Phenoxypyrrolidin-3-ol

Product 1

HCID 13320306Trans-1-(4-fluorophenyl)-3-(3-hydroxy-4-phenoxy-1-pyrrolidinyl)-1-propanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3.6 g. (0.02 mole) of 4-phenoxy-3-pyrrolidinol, 5 g. (0.0215 mole) of β-dimethylamino-p-fluoropropiophenone hydrochloride, 10 g. of potassium carbonate and 50 ml. of dimethylformamide was heated with stirring at 70° C. for 6 hr. while nitrogen gas was bubbled through the reaction mixture. The mixture was poured into water and extracted twice with benzene. The combined extracts were dried over anhydrous sodium sulfate and concentrated to give 6.1 g. of an oil as residue. The oil was chromatographed on 130 g. of silica gel. The desired compound was eluted with 20% acetone in benzene and 2.6 g. (39%) of an oil which gradually crystallized upon standing was obtained. This solid was recrystallized from petroleum ether diethylether to yield a white solid, m.p. 77°-80° C.

Workup

  1. additionA mixture of 3.6 g
  2. customwhile nitrogen gas was bubbled through the reaction mixture
  3. additionThe mixture was poured into water
  4. extractionextracted twice with benzene
  5. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto give 6.1 g
  8. customThe oil was chromatographed on 130 g
  9. washThe desired compound was eluted with 20% acetone in benzene and 2.6 g
  10. custom(39%) of an oil which gradually crystallized
  11. customupon standing was obtained
  12. customThis solid was recrystallized from petroleum ether diethylether
  13. customto yield a white solid, m.p. 77°-80° C.

Sources & evidence

ORD record
ord-9a48fba82529470a83c5cd69370247b0
Source dataset
uspto-grants-1986_04
Patent number
US04585785

Reaction notes

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