Benzo(b)thiophene, 3-bromo- → HCID 18930336, compound

HRID 1491695Notes

Reaction equation

HRID 1491695 reaction equation
C([Li])CCC.Br[C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1.[C:16]1([CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([CH:30]=[O:31])[CH2:26][CH2:25]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCCCCC.C(OCC)C>[C:16]1([CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([CH:30]([C:7]3[C:8]4[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=4[S:10][CH:11]=3)[OH:31])[CH2:26][CH2:25]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 123250Benzo(b)thiophene, 3-bromo-HCID 15681286HCID 15681286, compoundHCID 178418339Butyllithium

Product 1

HCID 18930336HCID 18930336, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve n-butyllithium (9.4 mL of a 2.5M solution in hexane, 23.46 mmol) in anhydrous ethyl ether (100 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, a solution of 3-bromobenzo[b]thiophene (5.0 g, 23.46 mmol) in anhydrous ethyl ether (50 mL). Stir at -78° C. for 30 minutes then add, by dropwise addition, a solution of 1-(2-phenylethyl)-4-piperidinecarboxaldehyde (5.10 g, 23.46 mmol) in anhydrous ethyl ether (50 mL). Stir for 5 hours at -78° C., remove the ice bath and stir for an additional 1 hour. Quench with saturated ammonium chloride (150 mL) and stir overnight. Separate the organic phase and extract the aqueous phase with ethyl ether and methylene chloride. Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by recrystallization (isopropanol) to give the title compound as an off-white solid.

Workup

  1. additionAdd, by dropwise addition
  2. additionthen add, by dropwise addition
  3. stirringStir for 5 hours at -78° C.
  4. customremove the ice bath
  5. stirringstir for an additional 1 hour
  6. customQuench with saturated ammonium chloride (150 mL)
  7. stirringstir overnight
  8. customSeparate the organic phase
  9. extractionextract the aqueous phase with ethyl ether and methylene chloride
  10. dry with materialdry (MgSO4)
  11. customevaporate the solvent in vacuo
  12. customPurify by recrystallization (isopropanol)

Sources & evidence

ORD record
ord-d3fafff081794718a0c9be299453aca5
Source dataset
uspto-grants-1994_12
Patent number
US05371093

Reaction notes

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