Hydrochloric Acid → 4-Hydroxy-1-methylpiperidine-4-carbonitrile

HRID 1734565Notes

Reaction equation

HRID 1734565 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.Cl.[C-:10]#[N:11].[K+]>O>[OH:8][C:5]1([C:10]#[N:11])[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 740491-Methyl-4-piperidone

Product 1

HCID 2840534-Hydroxy-1-methylpiperidine-4-carbonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

To freshly distilled 1-methylpiperidin-4-one (81.72 g, 0.72 mole) in water (200 cc), were added about 100 cc HCl 37% to pH 3. The reaction mixture was cooled in an ice bath and potassium cyanide (49 g, 0.75 mole) in water (200 cc) was added at an adequate rate in order to maintain an internal temperature of about 10° C. The reaction was stirred two hours more after the addition and then filtered. After washing with water and drying, the product, 4-hydroxy-4-cyano-1-methylpiperidine, was obtained in 67% yield as a white powder (67 g, 0.48 mole, mp. 135° C.).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. additionmore after the addition
  3. filtrationfiltered
  4. washAfter washing with water
  5. customdrying

Sources & evidence

ORD record
ord-eb0b82aade02403387005403ea3040cf
Source dataset
uspto-grants-1996_07
Patent number
US05534520

Reaction notes

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