Hexahydro-1,4-diazepine → HCID 131716943, Verbindung

HRID 1086450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1086450
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([S:15]([Cl:18])(=[O:17])=[O:16])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1.[NH:19]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(Cl)Cl>[ClH:18].[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([S:15]([N:19]4[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)(=[O:17])=[O:16])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 68163Hexahydro-1,4-diazepineHCID 19826025HCID 19826025, Verbindung

Produkt 1

HCID 131716943HCID 131716943, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Add the product of step 1 (1.0 g, 2.9 mmol) in methylene chloride (10 mL) dropwise over 10 minutes to hexahydro-2H-1,4-diazepine (0.35 g) in methylene chloride (20 mL). Stir for 18 hours. Partition the reaction mixture between ethyl acetate (75 mL) and hydrochloric acid (75 mL, 1N). Separate, and adjust the pH of the aqueous layer to alkaline pH (phenolphthalein indicator) with aqueous sodium hydroxide (1N) forming a heavy precipitate. Extract the reaction mixture with methylene chloride (100 mL), wash with saturated aqueous sodium bicarbonate (100 mL), saturated aqueous sodium chloride (100 mL). Dry (MgSO4), filter and concentrate in vacuo to give the title compound free base (0.87 g) as a light yellow solid. Rf=0.52 (450:45:5 methylene chloride:methanol:acetic acid). Chromatograph the free base (120 mg) on a column of silica gel (300 g, 60 micron particle size) eluting with 1:9 methanol:methylene chloride to give a solid. Dissolve the solid in hydrochloric acid (10 mL) and concentrate to give the title compound (110 mg) as a white solid, as the semihydrate. Calculated for C18H21O2.5N2SBrCl: C, 47.76; H, 4.68; N, 6.18. Observed: C, 47.76; H, 4.39; N, 6.14.

Aufarbeitung

  1. customPartition the reaction mixture between ethyl acetate (75 mL) and hydrochloric acid (75 mL, 1N)
  2. customSeparate
  3. customforming a heavy precipitate
  4. extractionExtract the reaction mixture with methylene chloride (100 mL)
  5. washwash with saturated aqueous sodium bicarbonate (100 mL), saturated aqueous sodium chloride (100 mL)
  6. dry with materialDry (MgSO4)
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5661cb62956d4479bf681613550bfc9f
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05030631

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