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

반응식

HRID 18428 반응식
[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

참가 물질

4

반응물 2

HCID 11617056N-[5-(3-cyanophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamideHCID 21226445Aluminium lithium hydride

생성물 1

HCID 11515729N-{5-[3-(aminomethyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide수율 100%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-614de7d5d184424bb381686a0dfdaff5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741351B2

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