Tetrahydrofuran → HCID 15086295, compound

HRID 1089760Notes

Reaction equation

HRID 1089760 reaction equation
[C:1]1(=O)[C:13]2[C:5]([C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:4][CH:3]=[CH:2]1.[CH3:15][N:16]1[CH2:21][CH2:20][CH:19]([Mg]Cl)[CH2:18][CH2:17]1.[Cl-].[NH4+].[O:26]1CCCC1>>[OH:26][C:12]1([CH:19]2[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]2)[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 22281833FluoreneoneHCID 178480358HCID 178480358, compound

Product 1

HCID 15086295HCID 15086295, compound

Procedure

A solution of 0.412 mol of fluorenone in 300 ml of tetrahydrofuran is added at 20° C. to a solution of 0.659 mol of (1-methyl-4-piperidyl)magnesium chloride in 600 ml of tetrahydrofuran. The mixture is left stirring overnight and then hydrolyzed in the cold state with ammonium chloride solution. The reaction medium is concentrated and the residue is taken up in one liter of water. The product is extracted with chloroform. The organic phase is dried over anhydrous sodium sulfate and then concentrated. After crystallization of the expected product, the latter is washed with ethyl ether and filtered off.

Workup

  1. waitThe mixture is left
  2. concentrationThe reaction medium is concentrated
  3. extractionThe product is extracted with chloroform
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customAfter crystallization of the expected product
  7. washthe latter is washed with ethyl ether
  8. filtrationfiltered off

Sources & evidence

ORD record
ord-8b7a9611ab8e45029cbd0cd6bc2c309a
Source dataset
uspto-grants-1992_01
Patent number
US05079249

Reaction notes

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