1,2-Dichloroethane → (4-Azido-phenyl)-(7-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-methanone

HRID 988978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 988978
[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]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 53255602-Azidobenzoic acidHCID 138533487-Methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine

Produkt 1

HCID 22250962(4-Azido-phenyl)-(7-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Versuchsvorschrift

7-Methoxy-2,3,4,5-tetrahydro-1 H-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.

Aufarbeitung

  1. washThe reaction was then washed with 10% citric acid, saturated sodium carbonate, and brine
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. customthe organic solvent removed under reduced pressure
  4. customThe material was then purified via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5ecdccf389194922a6805571a74f24b0
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638927B2

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