Реакция #51457

Уравнение реакции

1,3-diaminopropane

4-(4-fluorophenoxy)benzenesulfonyl chloride

→

N-(3-aminopropyl)-4-(4-fluorophenoxy)benzenesulfonamide

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   workup.ADDITIONafter the addition
2. 2
   Другоеpartitioned between ethyl acetate and water
3. 3
   workup.ADDITIONThe resulting emulsion was cleared by addition of dichloromethane
4. 4
   Другоеthe organic layer was separated
5. 5
   ЭкстракцияThe aqueous layer was extracted with dichloromethane
6. 6
   Экстракцияthe combined organic layers were extracted with 0.5 N aq. sodium bisulfate
7. 7
   Экстракцияextracted with dichloromethane (3×100 mL)
8. 8
   СушкаThe combined organic layers were dried over sodium sulfate
9. 9
   Концентрированиеconcentrated to a volume of about 50 mL
10. 10
    workup.ADDITIONAddition of hexane resulting in formation of a precipitate, which
11. 11
    Фильтрацияwas collected by filtration

Методика

To a stirred solution of 1,3-diaminopropane (6.7 mL) in 100 mL of dichloromethane at −10° C. was slowly added over a 2 hour period a solution of 4-(4-fluorophenoxy)benzenesulfonyl chloride (5.7 g, 20 mmol) in 50 mL of dichloromethane. The reaction was stirred for 15 minutes after the addition was complete, and then partitioned between ethyl acetate and water. The resulting emulsion was cleared by addition of dichloromethane, and the organic layer was separated. The aqueous layer was extracted with dichloromethane and the combined organic layers were extracted with 0.5 N aq. sodium bisulfate. The aqueous phase was brought to pH 8 with sodium bicarbonate and then extracted with dichloromethane (3×100 mL). The combined organic layers were dried over sodium sulfate and concentrated to a volume of about 50 mL. Addition of hexane resulting in formation of a precipitate, which was collected by filtration to provide N-(3-aminopropyl)-4-(4-fluorophenoxy)benzenesulfonamide (4.27 g) as a white solid: mp 184° C. (softens), 237° C. (melts) 1H NMR (300 MHz, DMSO-d6): δ 7.84 (d, J=9 Hz, 2H), 7.38-7.21 (m, 4H), 7.12 (d, J=9 Hz, 2H), 3.6-3.2 (br s, 3H), 2.80 (dd, J=7, 7 Hz, 2H), 2.77 (dd, J=7, 7 Hz, 2H), 1.72-1.60 (m, 2H).

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