Hydrochloric Acid → 7-iodo-2,3,4,5-tetrahydro-1H-2-benzazepine

Temperatur

75 °C

7-Iodo-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one (Preparation 1) (550 mg, 1.916 mmol) was dissolved in dry THF (70 ml) and treated with borane-THF complex (1M) (11.49 ml, 11.49 mmol) and heated at reflux for 4 hours. Then the reaction was left standing overnight. Additional borane-THF complex (1M, 2 ml) was added and the reaction heated at reflux temperature for a further 2 hours and 30 minutes. Methanol was carefully added to the cooled reaction mixture. The reaction was stirred until fizzing stopped. Then 2N HCl (aq) (20 ml) was carefully added portion-wise and, after fizzing had subsided, the solution heated at 75° C. for 30 minutes. LC/MS showed one major product. The reaction mixture was cooled and water was added (20 ml). The mixture was washed with EtOAc (40 ml), basified with 2 N NaOH (aq) and extracted with EtOAc (50 ml). The EtOAc layer was dried over anhydrous MgSO4 and evaporated to yield the title compound (400 mg) as a white solid. MS (ES) C10H12IN requires 273: found 274 (M+H)+.

1. additiontreated with borane-THF complex (1M) (11.49 ml, 11.49 mmol)
2. temperatureheated
3. temperatureat reflux for 4 hours
4. waitThen the reaction was left
5. additionAdditional borane-THF complex (1M, 2 ml) was added
6. temperaturethe reaction heated
7. temperatureat reflux temperature for a further 2 hours
8. custom30 minutes
9. temperatureThe reaction mixture was cooled
10. washThe mixture was washed with EtOAc (40 ml)
11. extractionextracted with EtOAc (50 ml)
12. dry with materialThe EtOAc layer was dried over anhydrous MgSO4
13. customevaporated

ORD-Eintrag

ord-b45a080242a547be8cb1a7467833a206

Quelldatensatz

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08222245B2