Guanidine Hydrochloride → HCID 178495361, Verbindung

HRID 1690614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690614
[Na].Cl.[NH2:3][C:4]([NH2:6])=[NH:5].[CH3:7][O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[C:17]([CH2:19][CH2:20][C:21](OCC)=[O:22])[CH:16]=[CH:15][C:14]=1[C:26]1[CH:31]=[CH:30][C:29]([CH2:32][N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)=[CH:28][CH:27]=1.[Cl:39]CCl.[Cl-].[Na+].O>C(O)C.CN(C=O)C>[ClH:39].[NH2:5][C:4](=[NH:6])[NH:3][C:21](=[O:22])[CH2:20][CH2:19][C:17]1[CH:16]=[CH:15][C:14]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:28][CH:27]=2)=[C:13]([O:12][CH2:11][CH2:10][CH2:9][O:8][CH3:7])[CH:18]=1

Komponenten

7

Edukt 4

HCID 5742Guanidine HydrochlorideHCID 5360545Sodium2×HCID 66906385Ethyl 3-[2-(3-methoxypropoxy)-4'-(piperidin-1-ylmethyl)biphenyl-4-yl]propanoateHCID 131726697Dichloromethane brine

Produkt 1

HCID 178495361HCID 178495361, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium (0.15 g, 6.4 mmol) was dissolved in ethanol (3.5 mL) at room temperature. Once all the sodium was dissolved, guanidine hydrochloride (0.61 g, 6.4 mmol) was added and the mixture was stirred for 1 h. A white precipitate formed and was filtered off. The filtrate was evaporated under reduced pressure and a solution of ethyl 3-[2-(3-methoxypropoxy)-4′-(piperidin-1-ylmethyl)biphenyl-4-yl]propanoate (0.45 g, 1.0 mmol) and DMF (3.5 mL) was added at room temperature. After completion of the reaction, the mixture was poured into: dichloromethane/brine (50/50). The aqueous layer was extracted three times with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was then dissolved in ethanol and HCl in diethyl ether (1N, 2 mL) was added. The mixture was evaporated and the residue was purified on reverse phase (C18) flash chromatography (H2O, HCl N/1000, acetonitrile, 100/0 to 80/20) to afford 0.23 g (43%) of the desired product as a white solid: mp=70° C.; 1H NMR (400 MHZ, d6-DMSO) δ 12.04 (bs, 1H), 10.12 (bs, 1H), 8.31 (bs, 2H), 7.56 (s, 4H), 7.22 (d, 1H), 7.00 (s, 1H), 6.91 (d, 1H), 4.22 (s, 2H), 4.01 (t. 2H), 3.35 (m, 6H), 3.21 (s, 3H), 2.93 (t, 2H), 2.87 (t, 2H), 1.90 (m, 2H), 1.76 (m, 6H).

Aufarbeitung

  1. customA white precipitate formed
  2. filtrationwas filtered off
  3. customThe filtrate was evaporated under reduced pressure
  4. customAfter completion of the reaction
  5. extractionThe aqueous layer was extracted three times with dichloromethane
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. dissolutionThe residue was then dissolved in ethanol
  11. additionHCl in diethyl ether (1N, 2 mL) was added
  12. customThe mixture was evaporated
  13. customthe residue was purified on reverse phase (C18) flash chromatography (H2O, HCl N/1000, acetonitrile, 100/0 to 80/20)

Quellen und Nachweise

ORD-Eintrag
ord-cd46150bd3c24213b8ffb0b30baf7d73
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153647B2

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