HCID 18930331, compound → alpha-[1-(2-Phenylethyl)-4-piperidinyl]-alpha-phenyl-2-benzo[b]thiophenemethanol

HRID 266097

Reaction equation

HRID 266097 reaction equation
[S:1]1[C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]2[CH:22]=[CH:23][CH:24]=[CH:25][C:2]1=2.[C:26]1([Li])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1.C1CCCCC1.C(OCC)C>[C:16]1([CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][CH:8]([C:6]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:5]3[S:1][C:2]4[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=4[CH:4]=3)[OH:7])[CH2:9][CH2:10]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 18930331HCID 18930331, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 18930373alpha-[1-(2-Phenylethyl)-4-piperidinyl]-alpha-phenyl-2-benzo[b]thiophenemethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21895417Cyclohexane diethyletherSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve [benzo[b]thiophene-2-yl][1-(2-phenylethyl)-4-piperidinyl]methanone (3.5 g, 10.01 mmol) in anhydrous tetrahydrofuran (100 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, phenyllithium (6 mL of a 2.0M solution in cyclohexane/ethyl ether, 12.0 mmol) and stir at -78° C. for 5 hours. Remove the ice bath and allow to warm to room temperature. Pour into saturated ammonium chloride (100 mL) and stir for 20 minutes. Separate the organic phase and extract the aqueous phase with ethyl acetate. Combine the organic phases, wash with water, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (50% ethyl acetate/hexane) and recrystallize (isopropanol) to give the title compound as a white solid; mp 144-°146° C.

Workup

  1. customRemove the ice bath
  2. temperatureto warm to room temperature
  3. additionPour into saturated ammonium chloride (100 mL)
  4. stirringstir for 20 minutes
  5. customSeparate the organic phase
  6. extractionextract the aqueous phase with ethyl acetate
  7. washwash with water
  8. dry with materialdry (MgSO4)
  9. customevaporate the solvent in vacuo
  10. customPurify by chromatography (50% ethyl acetate/hexane)
  11. customrecrystallize (isopropanol)

Sources & evidence

ORD record
ord-0c77f6a877e1492fae78aaf9ed602a09
Source dataset
uspto-grants-1997_07
Patent number
US05650416

Linked notes

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