تفاعل #353280

معادلة التفاعل

1-(2-phenylethyl)-4-piperidinecarboxaldehyde

n-butyllithium

3-bromobenzo[b]thiophene

→

title compound

α-[1-(2-Phenylethyl)-4-piperidinyl]-3-benzo[b]thiophenemethanol

المذيبات

ethyl ether

ethyl ether

hexane

ethyl ether

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAdd, by dropwise addition
2. 2
   workup.ADDITIONthen add, by dropwise addition
3. 3
   workup.STIRRINGStir for 5 hours at -78° C.
4. 4
   أخرىremove the ice bath
5. 5
   workup.STIRRINGstir for an additional 1 hour
6. 6
   أخرىQuench with saturated ammonium chloride (150 mL)
7. 7
   workup.STIRRINGstir overnight
8. 8
   أخرىSeparate the organic phase
9. 9
   استخلاصextract the aqueous phase with ethyl ether and methylene chloride
10. 10
    تجفيفdry (MgSO4)
11. 11
    أخرىevaporate the solvent in vacuo
12. 12
    أخرىPurify by recrystallization (isopropanol)

الإجراء التجريبي

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.

المصدر