Sodium hydride → 3-(6,7,8,9-Tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-propylamine
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[N:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])=[CH:7][CH:6]=1.[H-].[Na+]>>[N:10]1[C:9]2[NH:15][CH2:14][CH2:13][CH2:12][CH2:11][C:8]=2[CH:7]=[CH:6][C:5]=1[CH2:4][CH2:3][CH2:2][NH2:1]Participants
3
Procedure
A mixture of 3-5 (3.0 g, 14.5 mmol) and NaH (1.7 g of a 60% weight dispersion in mineral oil, 47 mmol) in xylenes (100 mL) was purged with argon for 30 min, and then heated at reflux for 72 hours. The mixture was cooled, quenched with ethanol, diluted with 10% aqueous potassium carbonate and extracted with ethyl acetate. The organics were dried over MgSO4 and concentrated to an oil. The residue was chromatographed on silica gel (15:10:1:1 EtOAc/EtOH/NH4OH/H2O) to give 800 mg of 3-6 as a yellow oil.
Workup
- customwas purged with argon for 30 min
- temperature