N-[5-(3-cyanophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide → N-{5-[3-(aminomethyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide

HRID 18428

Reaktionsgleichung

Reaktionsgleichung von HRID 18428
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[CH2:20][CH:19]([NH:24][S:25]([CH:28]([CH3:30])[CH3:29])(=[O:27])=[O:26])[CH2:18]3)[CH:12]=[CH:13][CH:14]=1)#[N:8]>O1CCCC1>[NH2:8][CH2:7][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[CH2:20][CH:19]([NH:24][S:25]([CH:28]([CH3:30])[CH3:29])(=[O:27])=[O:26])[CH2:18]3)[CH:12]=[CH:13][CH:14]=1

Komponenten

4

Versuchsvorschrift

A 1.0M solution of lithium aluminium hydride in tetrahydrofuran (8 ml) was cooled to 0° C. in an ice/methanol bath with stirring under argon. The solution was then treated dropwise with a solution of N-[5-(3-cyanophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (0.67 g, 1.97 mmol) in dry tetrahydrofuran (20 ml) over 15 mins. The cooling bath was removed and the whole mix stirred at reflux for 2 h. The reaction mix was allowed to cool to room temperature and quenched with water (0.8 ml), 10% NaOH (0.8 ml), and water again (1.2 ml). The reaction mix was dried over sodium sulphate, filtered and the filtrate evaporated under reduced pressure to give the title compound as a yellow oil (0.67 g, 100%).

Aufarbeitung

  1. customThe cooling bath was removed
  2. additionthe whole mix
  3. stirringstirred
  4. temperatureat reflux for 2 h
  5. additionThe reaction mix
  6. customquenched with water (0.8 ml), 10% NaOH (0.8 ml), and water again (1.2 ml)
  7. additionThe reaction mix
  8. dry with materialwas dried over sodium sulphate
  9. filtrationfiltered
  10. customthe filtrate evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-614de7d5d184424bb381686a0dfdaff5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741351B2

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