Hydrochloric Acid → HCID 18945118、化合物

HRID 400061

反応式

HRID 400061 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]#[N:9])=[CH:3][CH:2]=1.Cl.[CH2:11]([N:18]([CH2:22][CH2:23]Cl)[CH2:19][CH2:20][Cl:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+].Cl.O1CCOCC1>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC>[ClH:21].[CH2:11]([N:18]1[CH2:22][CH2:23][C:7]([C:8]#[N:9])([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 2777881N,N-Bis(2-chloroethyl)benzylamine hydrochlorideHCID 41120852-(Pyridin-4-yl)acetonitrile

生成物 1

HCID 18945118HCID 18945118、化合物

試薬・触媒・溶媒 1

HCID 84716Hexadecyltributylphosphonium bromide触媒

反応条件

温度
100 °C

実験手順

Combine 4-pyridylacetonitrile (19.4 g, 125 mmol), N-benzyl-N,N-bis-(2-chloroethyl)amine hydrochloride (33.6 g, 125 mmol), and hexadecyltributylphosphonium bromide (3 g, 6 mmol) and a 50% aqueous sodium hydroxide solution. Heat to 100° C. After 1 hour, cool the reaction mixture to ambient temperature and repeatedly extract with diethyl ether. Extract the combined organic layers twice with an aqueous 10% hydrochloric acid solution (350 mL). Combine the aqueous layers and neutralize with an aqueous 50% sodium hydroxide solution. Again extract three times with diethyl ether, combine the organic layers, dry over MgSO4, and filter. Add a solution of hydrochloric acid in dioxane (60 mL 4M, 240 mmol) and evaporate in vacuo to give 1-benzyl-4-cyano-4-(pyridin-4-yl)-piperidine hydrochloride.

後処理

  1. temperaturecool the reaction mixture to ambient temperature
  2. extractionrepeatedly extract with diethyl ether
  3. extractionExtract the combined organic layers twice with an aqueous 10% hydrochloric acid solution (350 mL)
  4. extractionAgain extract three times with diethyl ether
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo

出典と根拠

ORDレコード
ord-a357332337714054ae8a42857444bccd
出典データセット
uspto-grants-1998_10
特許番号
US05824690

関連ノート

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