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

HRID 343497

Reaction equation

HRID 343497 reaction equation
[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

Participants

9

Reactant 6

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f7969df0790a4ae481bb3fbccad1625b
Source dataset
uspto-grants-1999_01
Patent number
US05861417

Linked notes

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