3-Pyridineacetonitrile → HCID 18945079, Verbindung

HRID 343531

Reaktionsgleichung

Reaktionsgleichung von HRID 343531
Cl.[Cl:2][CH2:3][CH2:4][N:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][CH2:7]Cl.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][C:23]#[N:24])[CH:17]=1>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.[OH-].[Na+]>[ClH:2].[CH2:9]([N:5]1[CH2:6][CH2:7][C:22]([C:18]2[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=2)([C:23]#[N:24])[CH2:3][CH2:4]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 2

HCID 809233-PyridineacetonitrileHCID 2777881N,N-Bis(2-chloroethyl)benzylamine hydrochloride

Produkt 1

HCID 18945079HCID 18945079, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 84716Hexadecyltributylphosphonium bromideKatalysatorHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

Combine N,N-bis-(2-chloroethyl)benzylamine hydrochloric acid salt (72.0 g, 269 mmol) and pyrid-3-ylacetonitrile (31.8 g, 269 mmol) and hexadecyltributylphosphonium bromide (6 g) in aqueous solution of sodium hydroxide (50% by weight, 400 mL). Heat on a steam bath and stir vigorously. After 1.5 hours, cool the reaction mixture to ambient temperature. Extract the reaction mixture three times with dichloromethane. Combine the organic layers and extract twice with an aqueous 10% hydrochloric acid solution. Combine the aqueous layers and make basic with an aqueous solution of sodium hydroxide (50% by weight). Extract the basified aqueous layer three times with diethyl ether. Dry the combined ether layers over MgSO4 and filter to give a filtrate. Purge the filtrate with hydrogen chloride (gas) to give a solid. Collect the solid by filtration and dry in vacuo at 65° C. to give 1-benzyl-4-(pyrid-3-yl)-4-cyanopiperidine hydrochloric acid salt.

Aufarbeitung

  1. temperatureHeat on a steam bath
  2. extractionExtract the reaction mixture three times with dichloromethane
  3. extractionextract twice with an aqueous 10% hydrochloric acid solution
  4. extractionExtract the basified aqueous layer three times with diethyl ether
  5. dry with materialDry the combined ether layers over MgSO4
  6. filtrationfilter
  7. customto give a filtrate
  8. customPurge the filtrate with hydrogen chloride (gas)
  9. customto give a solid
  10. customCollect the solid
  11. filtrationby filtration
  12. customdry in vacuo at 65° C.

Quellen und Nachweise

ORD-Eintrag
ord-9efe00ab701e4604b3554c8bffb5a1ab
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05861417

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