N-(5-Cyano-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide → N-(5-aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide

HRID 492085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 492085
[C:1]([CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:6]=[CH:5][C:4]1=2)#[N:2]>O1CCCC1>[NH2:2][CH2:1][CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([NH:13][S:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)(=[O:16])=[O:15])[CH:6]=[CH:5][C:4]1=2

Komponenten

3

Edukt 1

HCID 68832042N-(5-Cyano-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide

Produkt 1

HCID 57678964N-(5-aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamideAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-(5-Cyano-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide(4.85 g, 15.5 mmol) was dissolved in 100 mL of dry tetrahydrofuran (THF), and the mixture was stirred while cooling in an ice bath. Borane-THF complex (40 mL, 1.0M) was added to the cold, stirring solution, and the reaction mixture was stirred under nitrogen for 15 hours at room temperature. The reaction mixture was quenched by addition of 20 mL of 20% HCl and 60 mL of methanol. The solvents were removed under reduced pressure, and the aqueous residue was treated dropwise with 1M NaOH until basic. The residue was extracted with EtOAc and the combined organic layers were dried (MgSO4) and evaporated. The crude product was acidified with dilute HCl in EtOH and recrystallized from EtOAc to yield 2.8 g of N-(5-aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide as a hydrochloride salt. MS: 317 (M+H)+.

Aufarbeitung

  1. temperaturewhile cooling in an ice bath
  2. additionBorane-THF complex (40 mL, 1.0M) was added to the cold
  3. stirringstirring solution
  4. stirringthe reaction mixture was stirred under nitrogen for 15 hours at room temperature
  5. customThe reaction mixture was quenched by addition of 20 mL of 20% HCl and 60 mL of methanol
  6. customThe solvents were removed under reduced pressure
  7. additionthe aqueous residue was treated dropwise with 1M NaOH until basic
  8. extractionThe residue was extracted with EtOAc
  9. dry with materialthe combined organic layers were dried (MgSO4)
  10. customevaporated
  11. customrecrystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-db22004ea61b4c71b1d433595f8ee153
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531577B2

Notizen zur Reaktion

Wird geladen…