HCID 10379653, compound → HCID 18930354, compound

HRID 266105Notes

Reaction equation

HRID 266105 reaction equation
[C:1]1([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH2:10]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li][C:24]1[S:25][CH:26]=[CH:27][CH:28]=1>O1CCCC1>[C:17]1([CH2:16][CH2:15][N:12]2[CH2:13][CH2:14][CH:9]([C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[OH:8])[CH2:10][CH2:11]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 10379653HCID 10379653, compoundHCID 178418439HCID 178418439, compound

Product 1

HCID 18930354HCID 18930354, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Dissolve phenyl[1-(2-phenylethyl)-4-piperidinyl]methanone (4.45 g, 15.16 mmol) in anhydrous tetrahydrofuran (40 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, 2-lithiothiophene (15.16 mL of a 1M solution in tetrahydrofuran, 15.16 mmol) and stir at -78° C. for 1.5 hours. Quench with saturated ammonium chloride, separate the organic phase and extract the aqueous phase with ethyl ether. Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (50% ethyl acetate/hexane) and recrystallize (cyclohexane) to give the title compound as a white crystalline solid; mp 143°-144° C.

Workup

  1. customQuench with saturated ammonium chloride
  2. customseparate the organic phase
  3. extractionextract the aqueous phase with ethyl ether
  4. dry with materialdry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customPurify by chromatography (50% ethyl acetate/hexane)
  7. customrecrystallize (cyclohexane)

Sources & evidence

ORD record
ord-58988884cc1843c1a7fe1f1222efeb66
Source dataset
uspto-grants-1997_07
Patent number
US05650416

Reaction notes

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