Hydrochloric Acid → 3-(3-(Biphenyl-4-ylmethylene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine dihydrochloride

HRID 1444747

Reaktionsgleichung

Reaktionsgleichung von HRID 1444747
[Cl-:1].[NH3+:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[NH+:11][CH:12]=[CH:13][CH:14]=1)=O.[Cl-].C(N(CC)C(C)C)(C)C.C([O-])(=O)C.[Na+].[C:30]1([C:36]2[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl>CO.C(O)(=O)C>[ClH:1].[ClH:1].[C:36]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:37]=[CH:38][C:39]([CH:40]=[C:6]2[CH2:5][CH2:4][CH2:3][N:2]=[C:7]2[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:42][CH:43]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 81531DiisopropylethylamineHCID 517045Sodium AcetateHCID 673376573-(5-Ammoniopentanoyl)pyridinium chloride

Produkt 1

HCID 673386073-(3-(Biphenyl-4-ylmethylene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-(5-Ammoniopentanoyl)pyridinium chloride (128 mg, 0.51 mmol) was suspended in methanol (2 mL) and treated with N,N-diisopropylethylamine (165 mg, 1.27 mmol) in a reaction vessel. This gave a clear solution. A dual solution of 0.6 M acetic acid and 0.3 M sodium acetate in methanol (10 mL) was then added, followed by addition of 4-phenylbenzaldehyde (140 mg, 0.76 mmol). The reaction vessel was then sealed and the reaction heated to 80 ° C. overnight then cooled to room temperature. The reaction mixture was then concentrated under reduced pressure, treated with a saturated solution of NaHCO3(aq), and extracted three times with EtOAc. The EtOAc extracts were washed with brine, then combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The recovered material was eluted through a 20 gram column of silica gel with 7:7:7:1:0.1 hexane:MtBE:CH2Cl2:MeOH:NH4OH eluant. One sample was recovered and dried under vacuum. This sample was then dissolved into MeOH and treated with two equivalents of 6 N HCl(aq), concentrated under reduced pressure and re-crystallized from isopropanol giving 80 mg (39%) of yellow needles. LC-MS: RT=5.72 min, [M+H]+ =325.1.

Aufarbeitung

  1. customThis gave a clear solution
  2. customThe reaction vessel was then sealed
  3. temperaturethen cooled to room temperature
  4. concentrationThe reaction mixture was then concentrated under reduced pressure
  5. additiontreated with a saturated solution of NaHCO3(aq)
  6. extractionextracted three times with EtOAc
  7. washThe EtOAc extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. washThe recovered material was eluted through a 20 gram column of silica gel with 7:7:7:1:0.1 hexane
  12. customOne sample was recovered
  13. customdried under vacuum
  14. dissolutionThis sample was then dissolved into MeOH
  15. concentrationconcentrated under reduced pressure
  16. customre-crystallized from isopropanol giving 80 mg (39%) of yellow needles

Quellen und Nachweise

ORD-Eintrag
ord-d43a3295814d480eb2cd3b064c639753
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662965B2

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