Bicarbonate Ion → methyl hexahydro-4-[[4-(phenylmethoxy)phenyl]methyl]-1H-1,4-diazepine-1-butanoate

HRID 16515

Reaktionsgleichung

Reaktionsgleichung von HRID 16515
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]3[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28].C(N(CC)CC)C.C(=O)(O)[O-]>C1COCC1>[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]3[CH2:22][CH2:21][CH2:20][N:19]([CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH2:18][CH2:17]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 769Bicarbonate IonHCID 8471TriethylamineHCID 107604Methyl 4-bromobutyrateHCID 11197238hexahydro-1-[[4-(phenylmethoxy)phenyl]methyl]-1H-1,4-diazepine

Produkt 1

HCID 68489685methyl hexahydro-4-[[4-(phenylmethoxy)phenyl]methyl]-1H-1,4-diazepine-1-butanoateAusbeute 79,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a manner similar as described above in Paragraph A, a solution of hexahydro-1-[[4-(phenylmethoxy)phenyl]methyl]-1H-1,4-diazepine (150 mg, 0.506 mmol) and methyl 4-bromobutanoate (0.29 mL, 2.0 mmol) in THF (6 mL) was treated with triethylamine (0.28 mL, 2 mmol) and the reaction was heated at reflux for 4 hours. The reaction was allowed to cool and treated with an aqueous bicarbonate solution. The combined ethyl acetate extracts were washed with water, dried and concentrated to give 0.16 g of methyl hexahydro-4-[[4-(phenylmethoxy)phenyl]methyl]-1H-1,4-diazepine-1-butanoate.

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 4 hours
  3. temperatureto cool
  4. washThe combined ethyl acetate extracts were washed with water
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bb0e708cf4c14bd1beb626c6497cc125
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737145B2

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