تفاعل #94378

معادلة التفاعل

4-(1-adamantyloxy)-2-fluoroaniline

1,4-dibromobutane

K2CO3

→

1-[4-(Adamantyloxy)-2-fluorophenyl]-pyrrolidine

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةis refluxed for 24 hours
2. 2
   أخرىThe solvent is evaporated
3. 3
   غسيلThe methylene chloride layer is washed with 2×125 ml of water
4. 4
   استخلاصthe combined aqueous portions are extracted with methylene chloride (50 ml)
5. 5
   تجفيفThe combined methylene chloride layers are dried
6. 6
   تركيزconcentrated
7. 7
   أخرىThe crude product is chromatographed by high pressure liquid chromatography on a 2.54 × 109 cm column at approximately 40 psi
8. 8
   غسيلeluting with 0.5% acetone in methylene chloride and collectint 200 ml fractions

الإجراء التجريبي

A mixture of 2.3 g (8.8 mmoles) of 4-(1-adamantyloxy)-2-fluoroaniline, 1.90 g (8.80 mmoles) of 1,4-dibromobutane, and 2.68 g (19.4 mmoles) of K2CO3 in deaerated absolute ethanol (25 ml) is refluxed for 24 hours. The solvent is evaporated, and the residue taken up in methylene chloride (125 ml) and water (125 ml). The methylene chloride layer is washed with 2×125 ml of water, and the combined aqueous portions are extracted with methylene chloride (50 ml). The combined methylene chloride layers are dried and concentrated. The crude product is chromatographed by high pressure liquid chromatography on a 2.54 × 109 cm column at approximately 40 psi, eluting with 0.5% acetone in methylene chloride and collectint 200 ml fractions. Fraction 3 contains 1.5 g of tan solid, m.p. 99.0°-105.9° C.

المصدر