Ammonia → 7-benzylamino-6,7-dihydro-5H-benzocyclohepten-2-ol

HRID 274058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274058
N([O-])=[O:2].[Na+].[CH2:5]([NH:12][CH:13]1[CH:19]=[CH:18][C:17]2[CH:20]=[C:21](N)[CH:22]=[CH:23][C:16]=2[CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N>S(=O)(=O)(O)O.O>[CH2:5]([NH:12][CH:13]1[CH:19]=[CH:18][C:17]2[CH:20]=[C:21]([OH:2])[CH:22]=[CH:23][C:16]=2[CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

6

Edukt 3

HCID 222AmmoniaHCID 23191869N7-benzyl-6,7-dihydro-5H-benzocyclohepten-2,7-diamineHCID 23668193Sodium Nitrite

Produkt 1

HCID 200947657-benzylamino-6,7-dihydro-5H-benzocyclohepten-2-olAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel2×

Versuchsvorschrift

Sodium nitrite (609 mg) aqueous solution (6 ml) was added dropwise to a stirred suspension of N7 -benzyl-6,7-dihydro-5H-benzocycloheptene-2,7-diamine (2.22 g) in 6N sulfuric acid (22 ml) under ice cooling over 15 minutes and the resulting solution was stirred at the same temperature for 30 minutes. The solution was added dropwise to a stirred solution of sulfuric acid (3 ml) in water (15 ml) at 75° C. over 15 minutes. The resulting mixture was stirred at the same temperature for 30 minutes, cooled with ice-water bath, basified with 28% ammonia solution (15 ml), and extracted six times with dichloromethane. The combined extracts were evaporated in vacuo and chromatographed over silica gel using dichloromethane and methanol to afford 7-benzylamino-6,7-dihydro-5H-benzocyclohepten-2-ol (1.72 g) as a pale brown oil.

Aufarbeitung

  1. stirringThe resulting mixture was stirred at the same temperature for 30 minutes
  2. temperaturecooled with ice-water bath
  3. extractionextracted six times with dichloromethane
  4. customThe combined extracts were evaporated in vacuo
  5. customchromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1fab16b4d4b0485c9c3a08db36b3902e
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387710

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