HCID 15681286, compound → HCID 18930330, compound

HRID 1736447Notes

Reaction equation

HRID 1736447 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH:15]=[O:16])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li][C:18]1[S:19][CH:20]=[CH:21][CH:22]=1>O1CCCC1>[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH:15]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[OH:16])[CH2:11][CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 15681286HCID 15681286, compoundHCID 178418439HCID 178418439, compound

Product 1

HCID 18930330HCID 18930330, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Dissolve 1-(2-phenylethyl)-4-piperidinecarboxaldehyde (10.0 g, 46.02 mmol) in anhydrous tetrahydrofuran (300 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, a solution of 2-lithiothiophene (46.02 mL of a 1M solution in tetrahydrofuran, 46.02 mmol) and stir for 3 hours at -78° C. Quench with saturated ammonium chloride, separate the organic phase and extract the aqueous phase with ethyl acetate. Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (ethyl acetate) and recrystallize (cyclohexane) to give the title compound as a white solid; mp 123°-125° C.

Workup

  1. additionAdd, by dropwise addition
  2. customQuench with saturated ammonium chloride
  3. customseparate the organic phase
  4. extractionextract the aqueous phase with ethyl acetate
  5. dry with materialdry (MgSO4)
  6. customevaporate the solvent in vacuo
  7. customPurify by chromatography (ethyl acetate)
  8. customrecrystallize (cyclohexane)

Sources & evidence

ORD record
ord-b18c4e86829e45f9b499ea1a9bb7990f
Source dataset
uspto-grants-1996_07
Patent number
US05541200

Reaction notes

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