تفاعل #171403

معادلة التفاعل

1-bromo-4-(3-bromopropoxy)benzene

4,4-difluoropiperidine hydrochloride

potassium carbonate

→

title compound

المردود 50.9%

1-[3-(4-bromophenoxy)propyl]-4,4-difluoropiperidine

المردود 50.9%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   تركيزconcentrated in vacuo
2. 2
   أخرىThe residue was partitioned between ether and saturated aqueous sodium bicarbonate
3. 3
   أخرىThe layers were separated
4. 4
   غسيلthe organic layer was washed with saturated aqueous sodium bicarbonate, water and brine
5. 5
   تجفيفThe organic layer was dried (Na2SO4)
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىPurification by flash column chromatography on an analogix SF40-80g column (hexanes/ethyl acetate=7:3)

الإجراء التجريبي

A suspension of 1-bromo-4-(3-bromopropoxy)benzene (1.85 g, 6.29 mmol), 4,4-difluoropiperidine hydrochloride (1.0 g, 6.34 mmol) and potassium carbonate (2.17 g, 15.7 mmol) in acetonitrile (100 mL) was heated to 60° C. overnight, then concentrated in vacuo. The residue was partitioned between ether and saturated aqueous sodium bicarbonate. The layers were separated; the organic layer was washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was dried (Na2SO4), filtered and concentrated. Purification by flash column chromatography on an analogix SF40-80g column (hexanes/ethyl acetate=7:3) afforded the title compound as a clear oil (1.07 g, 50%). LCMS m/z 334.3 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.90-2.08 (m, 6 H) 2.47-2.64 (m, 6 H) 3.99 (t, J=6.34 Hz, 2 H) 6.75-6.81 (m, 2 H) 7.34-7.40 (m, 2 H).

المصدر