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

HRID 343497

반응식

HRID 343497 반응식
[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

참가 물질

9

반응물 6

HCID 313Hydrochloric Acid2회HCID 8794PhenylacetonitrileHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 2777881N,N-Bis(2-chloroethyl)benzylamine hydrochlorideHCID 21951238Triethyl(hexadecyl)phosphanium bromide

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f7969df0790a4ae481bb3fbccad1625b
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05861417

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