Tetrahydrofuran → HCID 12515637, compound

HRID 1449060Notes

Reaction equation

HRID 1449060 reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][N:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:22]1[CH2:26][CH2:25][CH2:24]C1.[CH:27]([Mg]Cl)([CH3:29])[CH3:28]>CCOCC>[C:16]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][N:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([C:26]3([OH:22])[CH2:7][CH2:8][N:9]([CH2:28][CH:27]([C:29]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:6]4[CH:1]=[CH:2][CH:3]=[CH:4][CH:5]=4)[CH2:24][CH2:25]3)[CH2:10]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 125156351-(2,2-Diphenylethyl)piperidin-4-oneHCID 178418918HCID 178418918, compound

Product 1

HCID 12515637HCID 12515637, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The solution of 4 parts of 1-(2,2-diphenylethyl)-4-piperidinone in 50 parts by volume of tetrahydrofuran is cooled in an ice bath with stirring. To this solution is added 9.8 parts by volume of 2.2 M solution of isopropylmagnesium chloride in ether, and the resultant mixture is stirred for about 75 minutes at 0° C., and then quenched with the careful addition of 50 parts by volume of 10% ammonium chloride solution. The organic layer is separated and the aqueous phase is extracted with additional ethyl ether. The combined organic fractions are dried and concentrated to give yellow oil. This oil is chromatographed on silica gel using 10% acetone-methylene chloride mixture as the eluant to give yellow glass which upon trituration with heptane and recrystallization from a minimal amount of 95% ethanol affords 1-(2,2-diphenylethyl)-3-[1-(2,2-diphenylethyl)-4-hydroxypiperidin-4-yl]-4-piperidinone, melting at about 125°-127° C. This compound is represented by the following structural formula ##STR37##

Workup

  1. customquenched with the careful addition of 50 parts by volume of 10% ammonium chloride solution
  2. customThe organic layer is separated
  3. extractionthe aqueous phase is extracted with additional ethyl ether
  4. customThe combined organic fractions are dried
  5. concentrationconcentrated
  6. customto give yellow oil
  7. customThis oil is chromatographed on silica gel using 10% acetone-methylene chloride mixture as the eluant
  8. customto give yellow glass which upon trituration
  9. customwith heptane and recrystallization from a minimal amount of 95% ethanol

Sources & evidence

ORD record
ord-6a4e81a27afa4585b1a9f420e8dbdcbb
Source dataset
uspto-grants-1980_02
Patent number
US04188485

Reaction notes

Loading…