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

HRID 1678318

반응식

HRID 1678318 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매2회

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2ca258813f814e0f9c863d2880d0fc26
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008499B2

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