Реакция #1462611

Уравнение реакции

N-Methylpiperazine

1-(trifluoroacetyl)indoline-5-sulfonyl chloride

NaOH

→

5-[(4-methylpiperazin-1-yl)sulfonyl]indoline

Растворители

dichloromethane

1,4-dioxane

methanol

Условия реакции

Обработка

1. 1
   КонцентрированиеThe brown-colored reaction mixture was concentrated
2. 2
   Другоеthe residue dried in vacuo
3. 3
   Другоеto give a tan solid
4. 4
   workup.ADDITIONA suspension of the solid
5. 5
   workup.STIRRINGstirred for 1 hour
6. 6
   КонцентрированиеThe mixture was concentrated
7. 7
   Фильтрацияfiltered
8. 8
   Другоеdried in vacuo
9. 9
   ДругоеThe resulting solid was then partitioned between saturated sodium chloride solution (200 mL) and ethyl acetate (4×100 mL)
10. 10
    СушкаThe organic layer was dried over sodium sulfate
11. 11
    Концентрированиеconcentrated

Методика

N-Methylpiperazine (4.41 mL, 39.7 mmol, 2.00 equiv) was added to a solution of 1-(trifluoroacetyl)indoline-5-sulfonyl chloride (1-6, 6.23 g, 19.9 mmol, 1 equiv) in dichloromethane (50 mL) at 23° C., and the resulting mixture was stirred for 45 minutes. The brown-colored reaction mixture was concentrated and the residue dried in vacuo to give a tan solid. A suspension of the solid in a mixture of 1,4-dioxane (130 mL) and methanol (35 mL) was then treated with aqueous 1N NaOH solution (81.6 mL, 81.6 mmol, 3.00 equiv) and stirred for 1 hour. The mixture was concentrated, and the resulting solids were suspended in diethyl ether (175 mL), filtered, and dried in vacuo. The resulting solid was then partitioned between saturated sodium chloride solution (200 mL) and ethyl acetate (4×100 mL). The organic layer was dried over sodium sulfate and concentrated to provide the 5-[(4-methylpiperazin-1-yl)sulfonyl]indoline (1-7) as a tan solid. 1H NMR (500 MHz, DMSO-d6) δ 7.26 (s, 1H), 7.25 (d, 1H, J=7.8 Hz), 6.52 (d, 1H, 8.1 Hz), 6.48 (s, 1H), 3.55 (t, 2H, J=8.8 Hz), 3.00 (t, 2H, J=8.54 Hz), 2.79 (br s,4H), 2.34 (br s, 4H), 2.13 (s, 3H).

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