1,2-Dichloroethane → (4-Azido-phenyl)-(7-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-methanone
Reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.[N:14]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1C(O)=O)=[N+:15]=[N-:16].C(Cl)CCl.CCN(C(C)C)C(C)C.C1C[O:42][CH2:41]C1>CN(C1C=CN=CC=1)C>[N:14]([C:17]1[CH:18]=[CH:22][C:23]([C:41]([N:9]2[CH2:10][CH2:11][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:13]=[CH:12][C:6]=3[CH2:7][CH2:8]2)=[O:42])=[CH:24][CH:25]=1)=[N+:15]=[N-:16]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
7-Methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1 equivalent) was dissolved in THF (0.1 M) along with azidobenzoic acid (1.5 equivalents), EDC (1.5 equivalents), DMAP (0.18 equivalents), and DIEA (1.5 equivalents). The reaction was stirred at room temperature overnight. The reaction was then washed with 10% citric acid, saturated sodium carbonate, and brine. The organic layer was then dried over sodium sulfate and the organic solvent removed under reduced pressure. The material was then purified via flash chromatography using 8% acetone/1% ammonia solution/petroleum spirit running solvent to give the title compound. (MH+) 323.2.
Workup
- washThe reaction was then washed with 10% citric acid, saturated sodium carbonate, and brine
- dry with materialThe organic layer was then dried over sodium sulfate
- customthe organic solvent removed under reduced pressure
- customThe material was then purified via flash chromatography
Sources & evidence
- ORD record
- ord-934662624998475283d244091759f70e
- Source dataset
- uspto-grants-2006_02
- Patent number
- US06995269B2
Reaction notes
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