Hydrochloric Acid → 4-Piperidinecarbonitrile, 4-phenyl-1-(phenylmethyl)-, hydrochloride (1:1)

HRID 343497

反応式

HRID 343497 の反応式
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl.[Cl:13][CH2:14][CH2:15][N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:17][CH2:18]Cl.[Br-].C([P+](CC)(CC)CC)CCCCCCCCCCCCCCC.Cl.[OH-].[K+]>CO.O>[ClH:13].[CH2:20]([N:16]1[CH2:17][CH2:18][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:8]#[N:9])[CH2:14][CH2:15]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

9

反応物 6

HCID 313Hydrochloric Acid2 回HCID 8794PhenylacetonitrileHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 2777881N,N-Bis(2-chloroethyl)benzylamine hydrochlorideHCID 21951238Triethyl(hexadecyl)phosphanium bromide

生成物 1

HCID 126520624-Piperidinecarbonitrile, 4-phenyl-1-(phenylmethyl)-, hydrochloride (1:1)

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

Combine phenylacetonitrile (40 mmol), and aqueous sodium hydroxide solution (60 mL, 50% by weight). Add N,N-bis(2-chloroethyl)benzylamine hydrochloric acid salt (11.28 g, 42 mmol) and hexadecyltriethyl phosphonium bromide (1.02 g, 2 mmol). Heat to 100° C and stir vigorously. After 1 hour, cool the reaction mixture to ambient temperature. Add water and acidify the diluted reaction mixture with an aqueous 6M hydrochloric acid solution. Extract the acidified reaction mixture with diethyl ether. Adjust the pH of the aqueous layer to about 12 using solid potassium hydroxide and extract with ethyl acetate. Separate the ethyl acetate layer, dry over MgSO4, filter, and evaporate invacuo to give a residue. Combine the residue and a solution of hydrochloric acid in methanol. Evaporate in vacuo to give 1-benzyl-4-phenyl-4-cyanopiperidine hydrochloric acid salt.

後処理

  1. temperaturecool the reaction mixture to ambient temperature
  2. extractionExtract
  3. customthe acidified reaction mixture with diethyl ether
  4. extractionextract with ethyl acetate
  5. customSeparate the ethyl acetate layer
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customevaporate invacuo
  9. customto give a residue
  10. customEvaporate in vacuo

出典と根拠

ORDレコード
ord-f7969df0790a4ae481bb3fbccad1625b
出典データセット
uspto-grants-1999_01
特許番号
US05861417

関連ノート

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