Hydrochloric Acid → HCID 18986116, compound

HRID 2396756Notes

Reaction equation

HRID 2396756 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OO.[C-:15]#[N:16].[Na+].Cl.C[OH:20]>O.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[C:15]([CH:11]1[CH2:12][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9][N:10]1[OH:20])#[N:16]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 887MethanolHCID 8929Sodium CyanideHCID 698734-Phenylpiperidine

Product 1

HCID 18986116HCID 18986116, compound

Reagents, catalysts & solvents 2

HCID 150191Sodium Tungstate DihydrateCatalystHCID 962WaterSolvent

Procedure

To a stirred solution of 4-phenylpiperidine (10 g, 0.062 mole) in methanol (30 mL), was added a solution of sodium tungstate dihydrate (0.82 g, 2.48 mmole) in water (7 mL). With stirring at 0°, hydrogen peroxide (30%, 13.9 mL, 0.136 mole) was added dropwise. After complete addition, the reaction mixture was stirred for an additional 3 hours, and then sodium cyanide (4.56 g, 0.093 mole) was added, followed by 4 N HCl (22 mL, 0.088 mole). The reaction mixture was stirred overnight during which time it warmed to room temperature. The solid was collected by filtration through glass sinter funnel, and the solution was neutralized to pH 7 and was extracted with dichloromethane. The organic extract was combined with the solid and dried over MgSO4 and evaporated. Flash column purification eluting with 40% ethyl acetate in hexane gave 2-cyano-1-hydroxy-4-phenylpiperidine(8.6 g).

Workup

  1. additionAfter complete addition
  2. stirringthe reaction mixture was stirred for an additional 3 hours
  3. stirringThe reaction mixture was stirred overnight during which time it
  4. filtrationThe solid was collected by filtration through glass sinter funnel
  5. extractionwas extracted with dichloromethane
  6. extractionThe organic extract
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customFlash column purification
  10. washeluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e19d7caadde34d68851868972ba9dfd7
Source dataset
uspto-grants-1996_02
Patent number
US05494919

Reaction notes

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